Imidazole → N-{4-[4-(2,4-Dimethyl-thiazol-5-yl)-pyrimidin-2-ylamino]-phenyl}-2-imidazol-1-yl-acetamide

HRID 599160Notes

Reaction equation

Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[N:18]=[C:17]([C:19]3[S:23][C:22]([CH3:24])=[N:21][C:20]=3[CH3:25])[CH:16]=[CH:15][N:14]=2)=[CH:8][CH:7]=1)=[O:4].[NH:26]1[CH:30]=[CH:29][N:28]=[CH:27]1>>[CH3:24][C:22]1[S:23][C:19]([C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:12][C:9]3[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[CH2:2][N:26]4[CH:30]=[CH:29][N:28]=[CH:27]4)=[CH:7][CH:8]=3)[N:18]=2)=[C:20]([CH3:25])[N:21]=1

Participants

Reactant 2

HCID 795Imidazole

HCID 9999443HCID 9999443, compound

Product 1

HCID 59809703N-{4-[4-(2,4-Dimethyl-thiazol-5-yl)-pyrimidin-2-ylamino]-phenyl}-2-imidazol-1-yl-acetamide

Procedure

By treatment of 2-chloro-N-{4-[4-(2,4-dimethyl-thiazol-5-yl)-pyrimidin-2-ylamino]-phenyl}-acetamide with 1H-imidazole. 1H-NMR (DMSO-D6) δ: 2.61 (s, 3H, CH3), 2.63 (s, 3H, CH3), 4.86 (s, 2H, CH2), 6.88 (s, 1H, Aryl-H), 7.04 (d, 1H, J=5.9 Hz, pyrimidinyl-H), 7.15 (s, 1H, Aryl-H), 7.50 (d, 2H, J=7.8 Hz, Ph-H), 7.62 (s, 1H, Aryl-H), 7.68 (d, 2H, J=7.8 Hz, Ph-H), 8.48 (d, 1H, J=5.4 Hz, pyrimidinyl-H), 9.60 (s, 1H, NH), 10.18 (brs, 1H, NH). MS (ESI+) m/z 406.02 [M+H]+ (C20H19N7OS requires 405.48).

Sources & evidence

ORD record: ord-d9db62b171c2443dbe56840d52228663
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897605B2

Reaction notes

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