6-[(Dimethylamino)methylene]-4,5,6,7-tetrahydro-1,4,4-trimethyl-7-oxo-1H-indazole-3-carboxylic acid ethyl ester → HCID 57531657, compound

HRID 875102Notes

Reaction equation

HRID 875102 reaction equation
CN([CH:4]=[C:5]1[C:13](=O)[C:12]2[N:11]([CH3:15])[N:10]=[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]=2[C:7]([CH3:22])([CH3:21])[CH2:6]1)C.[Cl:23][C:24]1[CH:25]=[C:26]([NH:37][C:38]([NH2:40])=[NH:39])[CH:27]=[CH:28][C:29]=1[N:30]1[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]1>CN(C)C=O.O>[Cl:23][C:24]1[CH:25]=[C:26]([NH:37][C:38]2[N:40]=[CH:4][C:5]3[CH2:6][C:7]([CH3:21])([CH3:22])[C:8]4[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:10][N:11]([CH3:15])[C:12]=4[C:13]=3[N:39]=2)[CH:27]=[CH:28][C:29]=1[N:30]1[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]1

Participants

5

Reactant 2

HCID 689343446-[(Dimethylamino)methylene]-4,5,6,7-tetrahydro-1,4,4-trimethyl-7-oxo-1H-indazole-3-carboxylic acid ethyl esterHCID 178480750n-[3-Chloro-4-(4-methylpiperazin-1-yl)phenyl]guanidine

Product 1

HCID 57531657HCID 57531657, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 6-[(dimethylamino)methylene]-1,4,4-trimethyl-7-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylate (0.50 g, 1.6 mmol) and N-[3-chloro-4-(4-methylpiperazin-1-yl)-phenyl]-guanidine (0.48 g, 1.8 mmol) in anhydrous dimethylformamide was heated to 100° C. and kept at this temperature for 37 hours. After cooling, the mixture was diluted with water (50 mL) and the resulting precipitate was collected by filtration and dried to give the title compound (0.72 g, 85% yield) as a yellow solid.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-dca876d672d64af78b3bc7642c113a3d
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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