[3-Bromo-1-(4-chloro-phenyl)-2-oxo-cyclohexyl]-acetonitrile → 5-[4-(4-Chloro-phenyl)-4-cyanomethyl-4,5,6,7-tetrahydro-benzothiazol-2-ylamino]-2-(4-methyl-imidazol-1-yl)-benzonitrile

HRID 2076012Notes

Reaction equation

HRID 2076012 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH2:18])=[S:17])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1)#[N:2].Br[CH:20]1[CH2:25][CH2:24][CH2:23][C:22]([CH2:33][C:34]#[N:35])([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[C:21]1=O>C(O)C>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([C:22]2([CH2:33][C:34]#[N:35])[C:21]3[N:18]=[C:16]([NH:15][C:5]4[CH:6]=[CH:7][C:8]([N:9]5[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]5)=[C:3]([CH:4]=4)[C:1]#[N:2])[S:17][C:20]=3[CH2:25][CH2:24][CH2:23]2)=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 67096126[3-Bromo-1-(4-chloro-phenyl)-2-oxo-cyclohexyl]-acetonitrileHCID 86624673[3-Cyano-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea

Product 1

HCID 577807125-[4-(4-Chloro-phenyl)-4-cyanomethyl-4,5,6,7-tetrahydro-benzothiazol-2-ylamino]-2-(4-methyl-imidazol-1-yl)-benzonitrileYield 46.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [3-cyano-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (39.4 mg, 0.15 mmol) and of [3-bromo-1-(4-chloro-phenyl)-2-oxo-cyclohexyl]-acetonitrile (50.0 mg, 0.15 mmol) in ethanol (2 mL) was heated to reflux under an atmosphere of nitrogen for 2 days. After cooling to room temperature the solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using dichloromethane/methanol/concentrated aqueous NH4OH solution (9:1:0.1 v/v/v) as eluent to yield the title compound (34 mg, 46%) as a yellow gum. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.41 (s, 1H), 7.95 (s, 1H), 7.89 (d, 1H), 7.69 (s, 1H), 7.31 (t, 2H), 7.12 (d, 2H), 7.00 (d, 1H), 3.23 (d, 1H), 3.02 (d, 1H), 2.73 (m, 2H), 2.31 (s, 3H), 2.17 (m, 1H), 1.88 (m, 2H), 1.60 (m, 1H).

Workup

  1. temperatureto reflux under an atmosphere of nitrogen for 2 days
  2. customwas evaporated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6bff3a02d5344f74b6e145fe0809e8ec
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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