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1H-Indazol-6-amine → 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid (4-{3-[(1H-indazol-6-ylamino)-methylene]-2-oxo-2,3-dihydro-1H-indole-6-carbonyl}-phenyl)-amide

HRID 2352788
Notes
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Reaction equation

HRID 2352788 reaction equation
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]4[N:24]([CH2:29][CH3:30])[N:25]=[C:26]([CH3:28])[CH:27]=4)=[O:22])=[CH:16][CH:15]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:31].[NH:32]1[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([NH2:41])[CH:39]=2)[CH:34]=[N:33]1>C1COCC1>[NH:32]1[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([NH:41][CH:2]=[C:3]3[C:11]4[C:6](=[CH:7][C:8]([C:12]([C:14]5[CH:15]=[CH:16][C:17]([NH:20][C:21]([C:23]6[N:24]([CH2:29][CH3:30])[N:25]=[C:26]([CH3:28])[CH:27]=6)=[O:22])=[CH:18][CH:19]=5)=[O:13])=[CH:9][CH:10]=4)[NH:5][C:4]3=[O:31])[CH:39]=2)[CH:34]=[N:33]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 814231H-Indazol-6-amineHCID 178463085HCID 178463085, compound

Product 1

HCID 732242562-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid (4-{3-[(1H-indazol-6-ylamino)-methylene]-2-oxo-2,3-dihydro-1H-indole-6-carbonyl}-phenyl)-amideYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A small screw cap test tube was charged with 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 15, 100 mg, 0.240 mmol) and THF (2 mL). To the resulting solution was added 1H-Indazol-6-ylamine (36 mg, 0.264 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature and concentrated in vacuo. The crude residue was purified over silica (5% MeOH/95% CHCl3) yielding 16% (20 mg, 0.038 mmol) of the title compound.

Workup

  1. customA small screw cap test tube
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified over silica (5% MeOH/95% CHCl3)

Sources & evidence

ORD record
ord-197f1e9c8fca4836956613ff17fd7d6c
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07749530B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes