Ammonia → 1,1-Dimethylethyl 4-(5-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-1H-indazol-1-yl)-1-piperidinecarboxylate

HRID 1988933Notes

Reaction equation

HRID 1988933 reaction equation
[CH:1]1([NH:4][C:5](=[O:22])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][N:17]=[CH:16]4)[CH:7]=2)[CH2:3][CH2:2]1.[H-].[Na+].CS(O[CH:30]1[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]1)(=O)=O.N>CN(C=O)C>[CH:1]1([NH:4][C:5]([C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[N:18]([CH:30]3[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]3)[N:17]=[CH:16]4)[CH:7]=2)=[O:22])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 24758Sodium hydrideHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 10469531N-cyclopropyl-3-(1H-indazol-5-yl)-4-methylbenzamide

Product 1

HCID 586565121,1-Dimethylethyl 4-(5-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-1H-indazol-1-yl)-1-piperidinecarboxylateYield 4.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-cyclopropyl-3-(1H-indazol-5-yl)-4-methylbenzamide (Example 17) (0.07 g) in dry DMF (3 ml) was treated with sodium hydride (60% oil dispersion, 0.014 g) under nitrogen. After 5 min 1,1-dimethylethyl 4-[(methylsulfonyl)oxy]-1-piperidinecarboxylate (0.08 g) was added and the mixture was stirred at room temp. for 18 h. 0.88 Ammonia (1 ml) was added and the mixture was concentrated under vacuum. The residue was purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (1:1) followed by reverse phase preparative Hplc to give the title compound (0.005 g).

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. customThe residue was purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-5c4b1f3275f7474cb9019b8e6784f737
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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