Ethyl isocyanate → N-Ethyl-4-(6-{5-[(ethylamino)carbonyl]-3-fluoro-2-methylphenyl}-1H-indazol-3-yl)-1-piperidinecarboxamide

HRID 2246637Notes

Reaction equation

HRID 2246637 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[CH2:6]([NH:8][C:9](=[O:33])[C:10]1[CH:15]=[C:14]([C:16]2[CH:24]=[C:23]3[C:19]([C:20]([CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[N:21][NH:22]3)=[CH:18][CH:17]=2)[C:13]([CH3:31])=[C:12]([F:32])[CH:11]=1)[CH3:7]>CN(C=O)C>[CH2:1]([NH:3][C:4]([N:28]1[CH2:29][CH2:30][CH:25]([C:20]2[C:19]3[C:23](=[CH:24][C:16]([C:14]4[CH:15]=[C:10]([C:9]([NH:8][CH2:6][CH3:7])=[O:33])[CH:11]=[C:12]([F:32])[C:13]=4[CH3:31])=[CH:17][CH:18]=3)[NH:22][N:21]=2)[CH2:26][CH2:27]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 178464891HCID 178464891, compound2×

Product 1

HCID 178464892N-Ethyl-4-(6-{5-[(ethylamino)carbonyl]-3-fluoro-2-methylphenyl}-1H-indazol-3-yl)-1-piperidinecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl isocyanate (6.5 μL) and N-ethyl-3-fluoro-4-methyl-5-[3-(4-piperidinyl)-1H-indazol-6-yl]benzamide (Intermediate 22, 30 mg) in DMF (3 mL) was stirred at room temperature under nitrogen for 30 min. The solvent was removed under vacuum and the residue was purified by preparative HPLC to give the title compound as a white solid (18 mg).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-6d6ebcb1217e452fb4b1d314821144b6
Source dataset
uspto-grants-2010_03
Patent number
US07687532B2

Reaction notes

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