N-Methylcyclohexylamine → HCID 69508896, compound

HRID 1354054Notes

Reaction equation

HRID 1354054 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][C@@H:6]([NH:21][C:22]1[C:27]([Br:28])=[CH:26][N:25]=[C:24](Cl)[N:23]=1)[C:7]1[CH:12]=[CH:11][C:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[CH:9][CH:8]=1)[CH3:2].[CH3:31][NH:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>CC(O)C>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][C@@H:6]([NH:21][C:22]1[C:27]([Br:28])=[CH:26][N:25]=[C:24]([N:32]([CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[CH3:31])[N:23]=1)[C:7]1[CH:12]=[CH:11][C:10]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 7514N-MethylcyclohexylamineHCID 86585188HCID 86585188, compound

Product 1

HCID 69508896HCID 69508896, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of (R)-3-(5-bromo-2-chloropyrimidin-4-ylamino)-3-(4-(tert-butyldimethylsiloxy)phenyl)propanoic acid ethyl ester (1.0 eq) and N-methylcyclohexylamine (10.0 eq) in iPrOH in a sealed tube was stirred at 130° C. for 5 h, and then the iPrOH was evaporated. The residue was partitioned between water and EtOAc, and then the EtOAc extracts were treated with MgSO4, filtered and evaporated. The residue was purified by flash chromatography on silica gel using 9:1 hexanes/EtOAc to give (R)-3-(5-bromo-2-(N-cyclohexyl-N-methylamino)pyrimidin-4-ylamino)-3-(4-(tert-butyldimethylsiloxy)phenyl)propanoic acid ethyl ester.

Workup

  1. customthe iPrOH was evaporated
  2. customThe residue was partitioned between water and EtOAc
  3. additionthe EtOAc extracts were treated with MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel using 9:1 hexanes/EtOAc

Sources & evidence

ORD record
ord-dbb6a01050d949f8abe6995875d9cd94
Source dataset
uspto-grants-2007_05
Patent number
US07223762B2

Reaction notes

Loading…