1,2-Dichloroethane → HCID 69939378, compound

HRID 1058246Notes

Reaction equation

HRID 1058246 reaction equation
C(Cl)CCl.[NH2:5][CH2:6][C:7]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:8]=1[CH2:9][CH:10]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH:11]([F:13])[F:12].[C:28]([N:35]1[CH2:42][CH2:41][CH2:40][C@H:36]1[C:37](O)=[O:38])([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[Cl:27][C:25]1[CH:24]=[CH:23][C:8]([CH2:9][CH:10]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH:11]([F:13])[F:12])=[C:7]([CH:26]=1)[CH2:6][NH:5][C:37](=[O:38])[C@@H:36]1[CH2:40][CH2:41][CH2:42][N:35]1[C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 181649HOAtHCID 18672430HCID 18672430, compound

Product 1

HCID 69939378HCID 69939378, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (0.402 g, 2.10 mmol) was added to a stirred mixture of N-{1-[2-(aminomethyl)-4-chlorobenzyl]-2,2-difluoroethyl}-N-(4-methoxyphenyl)amine (0.550 g, 1.61 mmol), N-Boc-L-proline (0.347 g, 1.61 mmol) and HOAT (0.286 g, 2.10 mmol) in DMF (2.8 mL). After 18 h the mixture was partitioned between EtOAc and water. The organic phase was washed with 1 M citric acid, saturated aqueous NaHCO3 and brine, dried (Na2SO4) and evaporated in vacuo to give N-(5-Chloro-2-{3,3-difluoro-2-[(4-methoxyphenyl)amino]propyl}benzyl)-1-tert-butoxycarbonyl-L-prolinamide (0.626 g) as an oil; MS m/z=538.4.

Workup

  1. customAfter 18 h the mixture was partitioned between EtOAc and water
  2. washThe organic phase was washed with 1 M citric acid, saturated aqueous NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-379475d525994fee971cca83e23b0107
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

Loading…