2-Bromo-2',5'-dimethoxyacetophenone → [4-(2,5-Dimethoxy-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

HRID 604880Notes

Reaction equation

HRID 604880 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[O:13][CH3:14])=O.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([NH:29][C:30]([NH2:32])=[S:31])[CH:20]=[CH:21][C:22]=1[N:23]1[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]1>C(OCC)C>[CH3:14][O:13][C:6]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=1[C:3]1[N:32]=[C:30]([NH:29][C:19]2[CH:20]=[CH:21][C:22]([N:23]3[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]3)=[C:17]([O:16][CH3:15])[CH:18]=2)[S:31][CH:2]=1

Participants

4

Reactant 2

HCID 709972-Bromo-2',5'-dimethoxyacetophenoneHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 86624679[4-(2,5-Dimethoxy-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amineYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The title compound was prepared in analogy to example 1 step e) from 88 mg (0.33 mmol) 2-bromo-2′,5′-dimethoxyacetophenon and 79 mg (0.3 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea. The crude reaction was diluted with diethyl ether and stirred for 15 minutes at room temperature. The product was filtered off and dried to yield 124 mg (98%) [4-(2,5-dimethoxy-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a light green solid. MS ISP (m/e): 423.2 (100) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.68 (s, 1H), 9.28 (s, 1H), 7.99 (s, 1H), 7.72 (s, 1H), 7.69 (d, 1H), 7.54 (s, 1H), 7.52 (d, 1H), 7.28 (d, 1H), 7.07 (d, 1H), 6.89 (dd, 1H), 3.92 (s, 3H), 3.88 (s, 3H), 3.75 (s, 3H), 2.34 (s, 3H).

Workup

  1. customThe crude reaction
  2. filtrationThe product was filtered off
  3. customdried

Sources & evidence

ORD record
ord-cbe090b3b0f146d0b12810553b6989e5
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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