Pyridine → [3,5-Difluoro-4-(6-oxa-3-aza-bicyclo[3.1.0]hex-3-yl)-phenyl]-carbamic acid benzyl ester

HRID 1814038Notes

Reaction equation

HRID 1814038 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:15])[CH:5]=[C:6]([F:14])[C:7]=1[N:8]1[CH2:13][CH:12]2[CH:10]([O:11]2)[CH2:9]1.N1C=CC=CC=1.Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>ClCCl>[CH2:26]([O:25][C:23](=[O:24])[NH:15][C:4]1[CH:5]=[C:6]([F:14])[C:7]([N:8]2[CH2:13][CH:12]3[CH:10]([O:11]3)[CH2:9]2)=[C:2]([F:1])[CH:3]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 22505002HCID 22505002, compound

Product 1

HCID 20770994[3,5-Difluoro-4-(6-oxa-3-aza-bicyclo[3.1.0]hex-3-yl)-phenyl]-carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3,5-Difluoro-4-(6-oxa-3-aza-bicyclo[3.1.0]hex-3-yl)-phenylamine (0.14 g, 0.66 mmol) was dissolved in dichloromethane (1.0 mL) and pyridine (0.11 mL, 1.32 mmol) and stirred at 0° C. Benzyl chloroformate (0.1 mL, 0.72 mmol) was added and the mixture was stirred at 0° C. for one hour. The reaction mixture was allowed to warm to room temperature, washed with water, brine and dried (MgSO4). The title compound was isolated by silica gel chromatography (0-1% MeOH-DCM) as a pale yellow solid.

Workup

  1. temperatureto warm to room temperature
  2. washwashed with water, brine
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-e68b39b9f779467ca5223b3c708ad646
Source dataset
uspto-grants-2005_04
Patent number
US06875784B2

Reaction notes

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