HCID 68934618, compound → HCID 57531737, compound

HRID 875103Notes

Reaction equation

HRID 875103 reaction equation
O[CH:2]=[C:3]1[C:11](=O)[C:10]2[N:9]([CH3:13])[N:8]=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6]=2[CH2:5][C:4]1([CH3:20])[CH3:19].[Cl:21][C:22]1[CH:23]=[C:24]([NH:35][C:36]([NH2:38])=[NH:37])[CH:25]=[CH:26][C:27]=1[N:28]1[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]1>CN(C)C=O.[Cl-].[Na+].O>[Cl:21][C:22]1[CH:23]=[C:24]([NH:35][C:36]2[N:38]=[CH:2][C:3]3[C:4]([CH3:20])([CH3:19])[CH2:5][C:6]4[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:8][N:9]([CH3:13])[C:10]=4[C:11]=3[N:37]=2)[CH:25]=[CH:26][C:27]=1[N:28]1[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]1

Participants

5

Reactant 2

HCID 68934618HCID 68934618, compoundHCID 178480750n-[3-Chloro-4-(4-methylpiperazin-1-yl)phenyl]guanidine

Product 1

HCID 57531737HCID 57531737, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of ethyl 6-(hydroxymethylene)-1,5,5-trimethyl-7-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylate (400 mg, 1.44 mmol) and N-[3-chloro-4-(4-methyl-piperazin-1-yl)-phenyl]-guanidine (424 mg, 1.58 mmol) in anhydrous dimethylformamide (5 mL) was heated at 10° C. for 3 hours. After cooling, the reaction mixture was poured into brine (50 mL) and extracted with ethyl acetate (50 mL×2). The extracts were collected, dried on Na2SO4 and evaporated to dryness. The crude material was purified by flash chromatography on silica gel eluted with dichloromethane/methanol 9:1 to give the pure title compound (240 mg, 33% yield).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (50 mL×2)
  3. customThe extracts were collected
  4. customdried on Na2SO4
  5. customevaporated to dryness
  6. customThe crude material was purified by flash chromatography on silica gel
  7. washeluted with dichloromethane/methanol 9:1

Sources & evidence

ORD record
ord-4d4f57d59d084824911ce062414f0323
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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