Iodoacetamide → HCID 57670071, compound

HRID 1894518Notes

Reaction equation

HRID 1894518 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([N:17]2[C@@:21]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)([CH3:22])[C@@:20]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)([CH3:30])[N:19]=[C:18]2[C:38]2[CH:39]=[N:40][C:41]([C:47]([CH3:50])([CH3:49])[CH3:48])=[CH:42][C:43]=2[O:44][CH2:45][CH3:46])=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].I[CH2:58][C:59]([NH2:61])=[O:60]>CN(C)C=O.C(OCC)(=O)C>[C:59]([CH2:58][N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([N:17]2[C@@:21]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)([CH3:22])[C@@:20]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)([CH3:30])[N:19]=[C:18]2[C:38]2[CH:39]=[N:40][C:41]([C:47]([CH3:50])([CH3:49])[CH3:48])=[CH:42][C:43]=2[O:44][CH2:45][CH3:46])=[O:16])[CH2:10][CH2:9]1)(=[O:60])[NH2:61]

Participants

6

Reactant 3

HCID 3727IodoacetamideHCID 11430Potassium CarbonateHCID 57670152HCID 57670152, compound

Product 1

HCID 57670071HCID 57670071, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carboxylic acid piperidin-4-yl amide (50.0 mg, 0.081 mmole, example 205) and potassium carbonate (22.4 mg, 0.162 mmole) in N,N-dimethylformamide (4 mL) was added iodoacetamide (29.8 mg, 0.162 mmole, Aldrich). The mixture was stirred at room temperature overnight and diluted with ethyl acetate, washed with water, brine and concentrated. The crude product was purified by flash column chromatography (silica gel, eluting with a gradient of 1-10% methanol in dichloromethane) to give the title compound (40.5 mg, 74% yield). HR-MS (ES, m/z) calculated for C36H45Cl2N6O3 [(M+H)+] 679.2925, observed 679.2924.

Workup

  1. washwashed with water, brine
  2. concentrationconcentrated
  3. customThe crude product was purified by flash column chromatography (silica gel
  4. washeluting with a gradient of 1-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-b7114ac9fe534a66ada1b36526ba6133
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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