Pyrazole-1-carboxamidine monohydrochloride → HCID 178512761, compound

HRID 1068955Notes

Reaction equation

HRID 1068955 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:18]3[C:13](=[N:14][CH:15]=[N:16][C:17]=3[NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[NH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1.Cl.[N:28]1([C:33](N)=[NH:34])C=CC=N1>CN(C=O)C>[Cl:26][C:22]1[CH:21]=[C:20]([NH:19][C:17]2[N:16]=[CH:15][N:14]=[C:13]3[NH:12][N:11]=[C:10]([NH:9][C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][NH:1][C:33]([NH2:34])=[NH:28])[CH:4]=4)[C:18]=23)[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 178509838HCID 178509838, compound

Product 1

HCID 178512761HCID 178512761, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 200 mg (0.537 mmol) of 3-(3aminomethyl-phenylamino)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (water content: 1.79%; see Step 90.5), 79 mg (0.539 mmol) of 1H-pyrazole-1-carbamidine monohydrochloride and 2 ml of DMF is stirred at RT for 65 hours and then concentrated by evaporation under a high vacuum. Crystallization of the residue from diethyl ether, filtration and washing the filter residue with diethyl ether yield 4-(3-chlorophenylamino)-3-(3-{guanidino-methyl}-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine.1.05 hydrochloride having a water content of 1.76%; m.p. 270° C. (decomp.).

Workup

  1. concentrationconcentrated by evaporation under a high vacuum
  2. customCrystallization of the residue
  3. filtrationfrom diethyl ether, filtration
  4. washwashing the filter residue with diethyl ether

Sources & evidence

ORD record
ord-95d910000d43417c84620a43b9328e26
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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