Diisopropylethylamine → HCID 178479422, compound

HRID 1068953Notes

Reaction equation

HRID 1068953 reaction equation
O.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:19]3[C:14](=[N:15][CH:16]=[N:17][C:18]=3[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[NH:13][N:12]=2)=[CH:6][CH:5]=1.Cl.[N:29]1([C:34](N)=[NH:35])C=CC=N1.C(N(C(C)C)C(C)C)C>CN(C=O)C>[ClH:27].[Cl:27][C:23]1[CH:22]=[C:21]([NH:20][C:18]2[N:17]=[CH:16][N:15]=[C:14]3[NH:13][N:12]=[C:11]([NH:10][C:7]4[CH:8]=[CH:9][C:4]([CH2:3][NH:2][C:34]([NH2:35])=[NH:29])=[CH:5][CH:6]=4)[C:19]=23)[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 178510043HCID 178510043, compound

Product 1

HCID 178479422HCID 178479422, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 500 mg (1.303 mmol) of 3-(4-aminomethyl-phenylamino)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine hydrate (see Step 77.5), 229 mg (1.562 mmol) of 1H-pyrazole-1-carbamidine monohydrochloride (Fluka), 202 mg (1.563 mmol) of N-ethyldiisopropylamine and 5 ml of DMF is stirred at RT for 7 hours and then concentrated by evaporation under a high vacuum. Crystallization of the residue from methanol, filtration and washing the filter residue with methanol yield 4-(3-chloro-phenyl-amino)-3-(4-{guanidino-methyl}-phenylamino)-1H-pyrazolo-[3,4-d]pyrimidine hydrochloride having a water content of 2.86%; m.p. 254-256° C.

Workup

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

Sources & evidence

ORD record
ord-694d274f907642eda6111337424fc400
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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