ChemicalBook CAS DataBase List (R)-methyl 1-isopropyl-7-(methylsulfonyl)-2-(4-(trifluoromethyl)pyrimidin-2-yl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylate

(R)-methyl 1-isopropyl-7-(methylsulfonyl)-2-(4-(trifluoromethyl)pyrimidin-2-yl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylate synthesis

5synthesis methods

Product Name:(R)-methyl 1-isopropyl-7-(methylsulfonyl)-2-(4-(trifluoromethyl)pyrimidin-2-yl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylate
CAS Number:1456704-59-8
Molecular formula:C21H22F3N5O4S
Molecular Weight:497.49

1456693-55-2 Synthesis

(R)-methyl 1-isopropyl-7-(methylsulfonyl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo [1,2-a]pyrazine-8-carboxylate

1456693-55-2
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33034-67-2 Synthesis

33034-67-2
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(R)-methyl 1-isopropyl-7-(methylsulfonyl)-2-(4-(trifluoromethyl)pyrimidin-2-yl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylate

1456704-59-8
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Yield:1456704-59-8 78%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in isopropyl alcohol at 150; for 2 h;Microwave irradiation;

Steps:

2.11

Step 11: A mixture of (R)-methyl l-isopropyl-7-(methylsulfonyl)-l,2,3,4- tetrahydrobenzo[4,5]imidazo[l,2-a]pyrazine-8-carboxylate (0.9 g, 2.56 mmol), 2-chloro-4- (trifluoromethyl)pyrimidine (1.0 g, 5.1 mmol, 2 eq.) and DIEA (1.0 g, 7.7 mmol, 3 eq.) in i- PrOH (6 mL) was stirred in a microvave oven at 150 °C for 2 h. TLC showed the starting material was consumed completely (PE : EtOAc = 3 : 1). The solvent was removed in vacuo at 40 °C, and the residue was purified by column chromatography on silica gel eluting with PE / EtOAc = 6 / 1 to give (R)-methyl l-isopropyl-7-(methylsulfonyl)-2-(4- (trifluoromethyl)pyrimidin-2-yl)-l,2,3,4-tetrahydrobenzo[4,5]imidazo[l,2-a]pyrazine-8- carboxylate (1.0 g, 78% yield) as a white solid.LC-MS m/z 498.1 [M+H]⁺. 1H NMR (CDC1₃ 300MHz): δ 8.52 (d, 7 = 4.8 Hz, 1H), 8.13 (s, 1H), 8.06 (s, 1H), 6.83 (d, 7 = 4.8 Hz, 1H), 6.06 (d, 7 = 7.8 Ηζ,ΙΗ), 5.39-5.28 (m, 1H), 4.33-4.24 (m, 1H), 4.20-4.12 (m, 1H), 3.93 (s, 3H), 3.77-3.65 (m, 1H), 3.39 (s, 3H), 2.52-2.38 (m, 1H), 1.25 (d, 7 = 6.9 Hz, 3H), 1.02 (d, 7 = 6.6 Hz, 3H).

References:

WO2013/138565,2013,A1 Location in patent:Page/Page column 43; 44

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1456704-59-8
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References

1456693-00-7 Synthesis

(R)-benzyl (1-((2,2-dimethoxyethyl)amino)-3-methyl-1-oxobutan-2-yl)carbamate

1456693-00-7
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1456704-59-8
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References

(R)-benzyl 2-isopropyl-3-oxo-3,4-dihydropyrazine-1(2H)-carboxylate

1456693-01-8
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References

2-Piperazinone, 3-(1-methylethyl)-, (3R)-

1240590-09-3
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1456704-59-8
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References

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(R)-methyl 1-isopropyl-7-(methylsulfonyl)-2-(4-(trifluoromethyl)pyrimidin-2-yl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazine-8-carboxylate synthesis