Methylamine → HCID 67148364, compound

HRID 2428126Notes

Reaction equation

HRID 2428126 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:12][C:13]1[CH:14]=[C:15]([CH2:20][C:21]([OH:23])=O)[CH:16]=[CH:17][C:18]=1[Cl:19])[CH:9]1[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][NH2:25]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:12][C:13]1[CH:14]=[C:15]([CH2:20][C:21](=[O:23])[NH:25][CH3:24])[CH:16]=[CH:17][C:18]=1[Cl:19])[CH:9]1[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 67148302HCID 67148302, compound

Product 1

HCID 67148364HCID 67148364, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a sol. of {3-[(tert-butoxycarbonyl-cyclopropyl-amino)-methyl]-4-chloro-phenyl}-acetic acid (4.30 g, 12.6 mmol) in CH2Cl2 (130 mL) was added 1-chloro-N,N-2-trimethylpropenyl amine (1.87 mL, 15.2 mmol), and the mixture was stirred for 60 min. Methylamine (2M in THF, 25.0 mL, 50.0 mmol) was added, and the mixture was stirred overnight. More CH2Cl2 was added, and the mixture was washed with water and brine, was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 7:3) yielded the title compound (2.01 g, 45%). LC-MS: tR=0.95 min; ES+: 325.30.

Workup

  1. stirringthe mixture was stirred overnight
  2. washthe mixture was washed with water and brine
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the crude by FC (EtOAc/heptane 7:3)

Sources & evidence

ORD record
ord-ac05a9a6630a47b18cbb4f7515b2f90d
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

Loading…