[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea → HCID 86624708, compound

HRID 604926Notes

Reaction equation

HRID 604926 reaction equation
Cl[CH:2]([C:15](=O)[CH3:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([NH:32][C:33]([NH2:35])=[S:34])[CH:23]=[CH:24][C:25]=1[N:26]1[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]1>C(O)C>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][C:2]2[S:34][C:33]([NH:32][C:22]3[CH:23]=[CH:24][C:25]([N:26]4[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]4)=[C:20]([O:19][CH3:18])[CH:21]=3)=[N:35][C:15]=2[CH3:16])=[CH:5][C:6]=1[C:11]([F:14])([F:13])[F:12]

Participants

4

Reactant 2

HCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thioureaHCID 86624709HCID 86624709, compound

Product 1

HCID 86624708HCID 86624708, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared in analogy to example 1 step e) from crude 2-chloro-1-(4-chloro-3-trifluoromethyl-phenyl)-butan-3-one and 53 mg (0.2 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea in ethanol (1 ml). The crude product was purified on silica gel with methylene chloride/methanol 9/1 yielding 87 mg (88%) of the title compound as a brown solid. MS ISP (m/e): 493.2/495.2 (100/35) (M+H)+. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.63 (s, 1H), 7.51 (s, 1H), 7.43 (d, 1H), 7.30 (d, 1H), 7.23 (s, 1H), 7.15 (d, 1H), 6.90 (d, 1H), 6.85 (s, 1H), 4.00 (s, 2H), 3.82 (s, 3H), 2.31 (s, 6H).

Workup

  1. customThe crude product was purified on silica gel with methylene chloride/methanol 9/1 yielding 87 mg (88%) of the title compound as a brown solid

Sources & evidence

ORD record
ord-7a4f097933984a6d9666cbfed67308e5
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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