Phenyl carbamate → phenyl 3-(1,1-difluoroethyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-ylcarbamate

HRID 871704Notes

Reaction equation

HRID 871704 reaction equation
[F:1][C:2]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:6]=1)([F:4])[CH3:3].[C:19](=[O:28])([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)N>>[F:1][C:2]([C:5]1[CH:9]=[C:8]([NH:10][C:19](=[O:28])[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:6]=1)([F:4])[CH3:3]

Participants

3

Reactant 2

HCID 69322Phenyl carbamateHCID 668758983-(1,1-difluoroethyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-amine

Product 1

HCID 67159635phenyl 3-(1,1-difluoroethyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-ylcarbamateYield 64%

Procedure

3-(1,1-difluoroethyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-amine was converted to the phenyl carbamate using the procedure for Example 282A Step 2. Purification using silica gel chromatography eluting with EtOAc/hexane (5-40%) afforded phenyl 3-(1,1-difluoroethyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-ylcarbamate in 64% yield. LC-MS (ESI) m/z 374 (M−H)−

Workup

  1. customPurification
  2. washeluting with EtOAc/hexane (5-40%)

Sources & evidence

ORD record
ord-16659e82168c46c6bc224527ce14fe1b
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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