Benzenamine, 3-chloro-, hydrochloride (1:1) → HCID 178507467, compound

HRID 1602247

Reaction equation

HRID 1602247 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:21](C#N)=[C:20]([N:24]=[CH:25][N:26]([CH3:28])C)[NH:19][N:18]=2)=[CH:13][CH:12]=1>CO>[NH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[C:21]3[C:20](=[N:24][CH:25]=[N:26][C:28]=3[NH:6][C:5]3[CH:7]=[CH:8][CH:9]=[C:3]([Cl:2])[CH:4]=3)[NH:19][N:18]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 67336Benzenamine, 3-chloro-, hydrochloride (1:1)HCID 178484262HCID 178484262, compound

Product 1

HCID 178507467HCID 178507467, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

With the exclusion of moisture, 62 mg (0.38 mmol) of 3-chloro-aniline hydrochloride (see Step 14.4) are added to 92 mg (0.36 mmol) of N'-[3-(4-amino-phenyl)-4-cyano-1H-pyrazol-5-yl]-N,N-dimethylformamidine in 1 ml of methanol and the reaction mixture is boiled under reflux for 28 hours. The light-yellow reaction solution is cooled, concentrated by evaporation and chromatographed (SiO2, methylene chloride/ethanol [10:1]). Crystallization from isopropanol yields 3-(4-amino-phenyl)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine; TLC: Rf =0.33 (methylene chloride:methanol=10:1); FAB-MS: (M)+ =336; HPLC: TRet (Grad20-100)=9.2, TRet (Grad5-40)=18.8.

Workup

  1. temperatureunder reflux for 28 hours
  2. temperatureThe light-yellow reaction solution is cooled
  3. concentrationconcentrated by evaporation
  4. customchromatographed (SiO2, methylene chloride/ethanol [10:1])
  5. customCrystallization from isopropanol

Sources & evidence

ORD record
ord-32e83acf70044d60afe7b9f0b645144e
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Linked notes

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