[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea → HCID 25106199, compound

HRID 604928Notes

Reaction equation

HRID 604928 reaction equation
Cl[CH:2]([C:12](=O)[CH3:13])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([Cl:11])[CH:5]=1.[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(O)C>[Cl:11][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[CH3:10])[CH2:3][C:2]1[S:31][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)=[N:32][C:12]=1[CH3:13]

Participants

4

Reactant 2

HCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thioureaHCID 82054508HCID 82054508, compound

Product 1

HCID 25106199HCID 25106199, 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-chloro-4-methyl-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 56 mg (64%) of the title compound as a brown solid. MS ISP (m/e): 439.3/440.3/441.2/442.2 (100/69/50/34) (M+H)+. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.62 (s, 1H), 7.18-7.15 (m, 3H), 7.13 (s, 1H), 6.98 (d, 1H), 6.88 (d, 1H), 6.85 (s, 1H), 3.91 (s, 2H), 3.83 (s, 3H), 2.33 (s, 3H), 2.28 (s, 3H), 2.27 (s, 3H).

Workup

  1. customThe crude product was purified on silica gel with methylene chloride/methanol 9/1 yielding 56 mg (64%) of the title compound as a brown solid

Sources & evidence

ORD record
ord-e15c10e44dc0498995871f9037ed67c8
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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