6-Chloronicotinoyl Chloride → tert-Butyl (3-{[(6-Chloropyridin-3-yl)carbonyl]amino}-1-phenyl-1H-pyrazol-4-yl)-carbamate

HRID 1173153Notes

Reaction equation

HRID 1173153 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[C:9]([NH2:19])=[N:10][N:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][N:23]=1>N1C=CC=CC=1.C(Cl)Cl>[Cl:21][C:22]1[N:23]=[CH:24][C:25]([C:26]([NH:19][C:9]2[C:8]([NH:7][C:6](=[O:20])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:12][N:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:10]=2)=[O:27])=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 27821656-Chloronicotinoyl ChlorideHCID 57717456tert-Butyl (3-Amino-1-phenyl-1H-pyrazol-4-yl)carbamate

Product 1

HCID 57717470tert-Butyl (3-{[(6-Chloropyridin-3-yl)carbonyl]amino}-1-phenyl-1H-pyrazol-4-yl)-carbamate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl(3-amino-1-phenyl-1H-pyrazol-4-yl)carbamate (100 mg, 0.364 mmol) in pyridine (500 μL) was added 6-chloronicotinoyl chloride (53 mg, 0.304 mmol) in CH2Cl2 (2 mL). After 6 hours of stirring at room temperature, the reaction mixture was filtered and the solvent concentrated. Formation of t-butyl(3-([(6-chloropyridin-3-yl)carbonyl]amino)-1-phenyl-1H-pyrazol-4-yl)carbamate (J) was confirmed by MS (ESI+): cal'd [M+H]+ 414.1, obs'd 414.1.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe solvent concentrated

Sources & evidence

ORD record
ord-f84bfd558b3e478cb54116341f55e5b1
Source dataset
uspto-grants-2010_11
Patent number
US07834026B2

Reaction notes

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