Methyl iodide → HCID 57670146, compound

HRID 1894437Notes

Reaction equation

HRID 1894437 reaction equation
[C:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[N:12]([C:32]([N:34]3[CH2:39][CH2:38][CH:37]([N:40]4[CH2:45][CH2:44][NH:43][C:42](=[O:46])[CH2:41]4)[CH2:36][CH2:35]3)=[O:33])[C@@:13]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)([CH3:24])[C@@:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)([CH3:16])[N:15]=2)=[C:7]([O:47][CH2:48][CH3:49])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:52]I>CN(C)C=O>[C:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[N:12]([C:32]([N:34]3[CH2:35][CH2:36][CH:37]([N:40]4[CH2:45][CH2:44][N:43]([CH3:52])[C:42](=[O:46])[CH2:41]4)[CH2:38][CH2:39]3)=[O:33])[C@@:13]([C:25]3[CH:26]=[CH:27][C:28]([Cl:31])=[CH:29][CH:30]=3)([CH3:24])[C@@:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)([CH3:16])[N:15]=2)=[C:7]([O:47][CH2:48][CH3:49])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57669959HCID 57669959, compound

Product 1

HCID 57670146HCID 57670146, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-{1-[(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-carbonyl]-piperidin-4-yl}-piperazin-2-one (61.8 mg, example 117) was dissolved in N,N-dimethylformamide (1 mL), sodium hydride (60% in mineral oil, 20 mg, Aldrich) was added. After stirring for 5 min, methyl iodide (0.03 mL, Aldrich) was added. The mixture was stirred at ambient temperature for 3 h, and the crude product was purified on a HPLC (reversed phase, eluting with acetonitrile and water) to give the title product (34 mg). HR-MS (ES, m/z) calculated for C39H49C12N6O3 [(M+H)+] 719.3238, observed 719.3242.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 3 h
  2. customthe crude product was purified on a HPLC (reversed phase, eluting with acetonitrile and water)

Sources & evidence

ORD record
ord-9501203cc4ea4bb2a843a1de67671315
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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