Cyclopropylamine → HCID 67148825, compound

HRID 2428124Notes

Reaction equation

HRID 2428124 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].[CH:24]1([NH2:27])[CH2:26][CH2:25]1>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:27][CH:24]2[CH2:26][CH2:25]2)[CH:16]=[CH:17][C:18]=1[Cl:19])[CH:9]1[CH2:10][CH2:11]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 67148302HCID 67148302, compound

Product 1

HCID 67148825HCID 67148825, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

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. A sol. of cyclopropylamine (3.62 mL, 50.6 mmol) in CH2Cl2 (50 mL) was added, and the mixture was stirred for 60 min. 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 (3.14 g, 65%). LC-MS: tR=0.97 min; ES+: 323.29.

Workup

  1. stirringthe mixture was stirred for 60 min
  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-9f0b22a8549b4c5992f0b1e7d467beb9
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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