Cyclopentylamine → HCID 58760954, compound

HRID 857481Notes

Reaction equation

HRID 857481 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[N:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[C:10]=1[CH:11]=O)=[O:5])[CH3:2].[CH:27]1([NH2:32])[CH2:31][CH2:30][CH2:29][CH2:28]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[N:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[C:10]=1[CH2:11][NH:32][CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86594821HCID 86594821, compound

Product 1

HCID 58760954HCID 58760954, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 2-(4-chloro-phenyl)-1-(2-fluoro-phenyl)-5-formyl-1H-imidazole-4-carboxylic acid ethyl ester I-5e-2 (1000 mg, 2.68 mmol), cyclopentylamine (251 mg, 2.95 mmol), NaBH(OAc)3 (796 mg, 3.76 mmol) in dichloroethane was stirred for 17 h at room temperature. The reaction was concentrated in vacuo and the residue was diluted with CHCl3. The organic solution was washed with sat'd aq. NaHCO3 and sat'd aq. NaCl, dried, and concentrated under vacuum. The crude residue was purified on SiO2-gel (Flash 40s) using a solvent gradient of 30% EtOAc/hexanes to 80% EtOAc/hexanes to give the desired product (I-5f) as a yellow oil (680 mg, 57%): +APCI MS (M+1) 442.2.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additionthe residue was diluted with CHCl3
  3. washThe organic solution was washed with sat'd aq. NaHCO3
  4. customdried
  5. concentrationconcentrated under vacuum
  6. customThe crude residue was purified on SiO2-gel (Flash 40s)

Sources & evidence

ORD record
ord-74985de3c0c3480888b83c0ff66eb9da
Source dataset
uspto-grants-2006_12
Patent number
US07145012B2

Reaction notes

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