2-Chlorocyclohexanone → HCID 25106201, compound

HRID 604888Notes

Reaction equation

HRID 604888 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([NH:23][C:24]([NH2:26])=[S:25])[CH:14]=[CH:15][C:16]=1[N:17]1[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]1>C(O)C>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([NH:23][C:24]2[S:25][C:2]3[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=3[N:26]=2)[CH:14]=[CH:15][C:16]=1[N:17]1[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]1

Participants

4

Reactant 2

HCID 132032-ChlorocyclohexanoneHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 25106201HCID 25106201, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared in analogy to example 1 step e) from 46 mg (0.33 mmol) 2-chlorocyclohexanon and 79 mg (0.3 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea in ethanol (3 ml). The crude product was purified on silica gel with methylene chloride/methanol 19/1 yielding 40 mg (39%) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-(4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine as a yellow solid. MS ISP (m/e): 341.4 (100) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.16 (s, 1H), 7.63 (s, 1H), 7.49 (s, 1H), 7.28 (d, 1H), 7.22 (d, 1H), 7.01 (s, 1H), 3.77 (s, 3H), 2.57 (br s, 4H), 2.14 (s, 3H), 1.71 (br s, 4H).

Workup

  1. customThe crude product was purified on silica gel with methylene chloride/methanol 19/1 yielding 40 mg (39%) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-(4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine as a yellow solid

Sources & evidence

ORD record
ord-dac92cef014f4f419e48eb373b916896
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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