HCID 67776061, compound → HCID 67776316, compound

HRID 1037529Notes

Reaction equation

HRID 1037529 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]([NH:19][CH3:20])=[O:18])=[C:15]3[C:10]([CH:11]=[C:12]([N+:24]([O-])=O)[C:13]([CH:21]4[CH2:23][CH2:22]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1>C1COCC1.CO.[Ni]>[NH2:24][C:12]1[C:13]([CH:21]2[CH2:23][CH2:22]2)=[CH:14][C:15]2[C:10]([CH:11]=1)=[N:9][N:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C:16]=2[C:17]([NH:19][CH3:20])=[O:18]

Participants

5

Reactant 1

HCID 67776061HCID 67776061, compound

Product 1

HCID 67776316HCID 67776316, compoundYield 83.7%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(4-chlorophenyl)-5-cyclopropyl-N-methyl-6-nitro-2H-indazole-3-carboxamide (127 mg, 0.34 mmol) in THF (2.5 mL) and MeOH (7.5 mL) was added Raney nickel (20 mg) and the reaction was stirred vigorously under an atmosphere of hydrogen at 60° C. for 2 h. The reaction mixture was diluted with MeOH (40 mL), filtered and then concentrated to dryness to give 6-amino-2-(4-chlorophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide as a tan solid (97 mg, 83%).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6cf51ca15703427880c06aec4351012a
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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