Ethyl isocyanate → HCID 57669897, compound

HRID 1894517Notes

Reaction equation

HRID 1894517 reaction equation
C(O[C:6]([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:7])(C)(C)C.[CH2:51]([N:53]=C=O)[CH3:52]>ClCCl>[CH2:51]([NH:53][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]([N:17]2[C@@:21]([C:23]3[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=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])([CH3:48])[CH3:49])=[CH:42][C:43]=2[O:44][CH2:45][CH3:46])=[O:16])[CH2:12][CH2:13]1)=[O:7])[CH3:52]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 57670152HCID 57670152, compound

Product 1

HCID 57669897HCID 57669897, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 (51.2 mg, 0.082 mmole, example 205) and ethyl isocyanate (12.0 mg, 0.169 mmole, Aldrich) in dichloromethane (4 mL) was stirred at room temperature for 2 h before concentrated to dryness. The residue was purified by flash column chromatography (silica gel, eluting with a gradient of 1-10% methanol in dichloromethane) to give the title compound (44.6 mg, 78% yield). HR-MS (ES, m/z) calculated for C37H47Cl2N6O3 [(M+H)+] 693.3081, observed 693.3081.

Workup

  1. concentrationbefore concentrated to dryness
  2. customThe residue was purified by flash column chromatography (silica gel
  3. washeluting with a gradient of 1-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8c321f649b304ab798837fb24b2b4b51
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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