[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea → HCID 25106198, compound

HRID 604927Notes

Reaction equation

HRID 604927 reaction equation
Cl[CH:2]([C:17](=O)[CH3:18])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]([F:16])([F:15])[CH:12]([F:14])[F:13])[CH:5]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([NH:34][C:35]([NH2:37])=[S:36])[CH:25]=[CH:26][C:27]=1[N:28]1[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]1>C(O)C>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([NH:34][C:35]2[S:36][C:2]([CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]([F:16])([F:15])[CH:12]([F:14])[F:13])[CH:5]=3)=[C:17]([CH3:18])[N:37]=2)[CH:25]=[CH:26][C:27]=1[N:28]1[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]1

Participants

4

Reactant 2

HCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thioureaHCID 86624710HCID 86624710, compound

Product 1

HCID 25106198HCID 25106198, 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-(3-(1,1,2,2-tetrafluoro-ethoxy)-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 98 mg (96%) of the title compound as a brown solid. MS ISP (m/e): 507.3 (100) (M+H)+. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.63 (s, 1H), 7.31 (t, 1H), 7.20 (s, 1H), 7.15-7.04 (m, 4H), 6.88 (d, 1H), 6.85 (s, 1H), 6.08-5.38 (tt, 1H), 3.99 (s, 2H), 3.81 (s, 3H), 2.28 (s, 6H).

Workup

  1. customThe crude product was purified on silica gel with methylene chloride/methanol 9/1 yielding 98 mg (96%) of the title compound as a brown solid

Sources & evidence

ORD record
ord-e9ccf4ec10e148a5b5c532717a1288b4
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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