Aniline → HCID 25107344, compound

HRID 604893Notes

Reaction equation

HRID 604893 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]3)=[C:14]([O:24][CH3:25])[CH:13]=2)[S:9][CH:10]=1)C.[F:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1.NC1C=CC=CC=1.C[Al](C)C>>[F:27][C:28]1[CH:34]=[CH:33][C:31]([NH:32][C:4](=[O:3])[CH2:5][C:6]2[N:7]=[C:8]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]4)=[C:14]([O:24][CH3:25])[CH:13]=3)[S:9][CH:10]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 4

HCID 6115AnilineHCID 97314-FluoroanilineHCID 16682925TrimethylaluminumHCID 86624685HCID 86624685, compound

Product 1

HCID 25107344HCID 25107344, compoundYield 89%

Procedure

The title compound was prepared in analogy to example 27 from 92 mg (0.25 mmol) ({2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazol-4-yl}-acetic acid ethyl ester and 98 mg (0.87 mmol) 4-fluoroaniline. After the first addition conversion was not complete. Therefore the same amount of the aniline and trimethylaluminium were added and the reaction was heated again over night. Workup as in example 27 and subsequent purification on silica gel with methylene chloride/methanol 19/1 yielded 95 mg (89%) N-(4-fluoro-phenyl)-2-{2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazol-4-yl}-acetamide as a brown oil. MS ISP (m/e): 438.1 (100) (M+H)+. 1H NMR (CDCl3, 250 MHz): δ (ppm)=9.08 (s, 1H), 7.65 (s, 2H), 7.45 (dd, 2H), 7.31 (s, 1H), 7.21 (d, 1H), 7.06-6.88 (m, 3H), 6.51 (s, 1H), 3.80 (s, 3H), 3.73 (s, 2H), 2.30 (s, 3H).

Workup

  1. temperaturethe reaction was heated again over night
  2. customWorkup as in example 27 and subsequent purification on silica gel with methylene chloride/methanol 19/1

Sources & evidence

ORD record
ord-0034b45fa8184f3891a8e4e45fa7a226
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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