2-Bromo-3'-chloro-4'-methylpropiophenone → [4-(3-Chloro-4-methyl-phenyl)-5-methyl-thiazol-2-yl]-[4-(4-methyl-imidazol-1-yl)-phenyl]-amine

HRID 604932Notes

Reaction equation

HRID 604932 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH2:16])=[S:15])=[CH:9][CH:8]=2)[CH:6]=1.Br[CH:18]([CH3:29])[C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([Cl:28])[CH:22]=1)=O>>[Cl:28][C:23]1[CH:22]=[C:21]([C:19]2[N:16]=[C:14]([NH:13][C:10]3[CH:9]=[CH:8][C:7]([N:5]4[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]4)=[CH:12][CH:11]=3)[S:15][C:18]=2[CH3:29])[CH:26]=[CH:25][C:24]=1[CH3:27]

Participants

3

Reactant 2

HCID 27749502-Bromo-3'-chloro-4'-methylpropiophenoneHCID 86624711[4-(4-Methyl-imidazol-1-yl)-phenyl]-thiourea

Product 1

HCID 86624714[4-(3-Chloro-4-methyl-phenyl)-5-methyl-thiazol-2-yl]-[4-(4-methyl-imidazol-1-yl)-phenyl]-amineYield 68%

Procedure

Prepared in analogy to example 64d) from 100 mg (0.43 mmol) [4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (example 72c)) and 124 mg (0.47 mmol) 2-bromo-3′-chloro-4′-methylpropiophenone. 115 mg (68%) of the product was isolated as a colorless solid. MS ISP (m/e): 395.1 (100) (M+H)+. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.50 (s, 1H), 9.47 (s, 1H), 7.95 (s, 1H), 7.87 (d, 2H), 7.70-7.60 (m, 3H), 7.52 (d, 2H), 2.45 (s, 3H), 2.41 (s, 3H), 2.35 (s, 3H).

Sources & evidence

ORD record
ord-b75e24c2ca324b04933abfeb852674c2
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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