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 44594Notes

Reaction equation

HRID 44594 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-methyl-piperazin-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-cded68617664494183d62a6b0c5ca562
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Reaction notes

Loading…