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ChemicalBook CAS DataBase List Afatinib Impurity 19
1245555-42-3

Afatinib Impurity 19 synthesis

1synthesis methods
-

Yield:-

Reaction Conditions:

in ISOPROPYLAMIDE;water at 0;

Steps:

A.1.1.1

To a stirred solution of the above crude (2E)-4-brorno-N-[4-(3-chloro-4-fluoroanilino)-7-methoxy- 6-quinazolinyl]-2-butenamide (1.0 g, 2.15 mmol) in dimethylacetamide (35 mL) at 0 °C was added excess aqueous dimethylamine solution (40 %, 5 mL). After 3 hours the reaction was diluted with brine and extracted with ethyl acetate (3x). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. Chromatography on silica gel elutingwith dichloromethane/methanol (5:95 to 15:85) then gave (2jE)-N-[4-(3-chloro-4- fluoroanilino)-7-methoxy-6-quinazolmyl]-4-(dirned3ylamino)-2-butenaniide (14) (0.74 g, 80%) as a white solid, m.p. (MeOH) 179-181°C. 1H NMR [(CDj)2SO] δ 9.78 (s, 1 H), 9.64 (s, 1 H), 8.93 (s, 1 H), 8.53 (s, 1 H), 8.13 (ddj = 2.6, 6.9 Hz, 1 H), 7.83-7.79 (m, 1 H), 7.42 (ddj = 9.1 Hz, JHF = 9.1 Hz, 1 H), 7.29 (s, 1 H), 6.80 (pi, J = 6.0, 15.4 Hz, 1 H), 6.58 (dj = 15.4 Hz, 1 H), 4.01 (s, 3 H), 3.08 (d J = 6.0 Hz, 2 H), 2.19 (s, 6 H). Analysis found: C, 56.32; H, 5.14; N, 15.73. C21H21ClFN5O2-H2O requires: C, 56.32; H, 5.18; N, 15.64.

References:

WO2010/104406,2010,A1 Location in patent:Page/Page column 34; 43-44

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