Hydrochloric Acid → HCID 178478809, compound

HRID 619267Notes

Reaction equation

HRID 619267 reaction equation
[ClH:1].[N:2]1([C:7](N)=[NH:8])C=CC=N1.Cl.Cl.[NH:12]1[C:16]2=[N:17][CH:18]=[CH:19][C:20]([NH:21][C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([CH2:29][NH2:30])=[CH:25][CH:24]=3)=[C:15]2[CH:14]=[N:13]1.C(N(C(C)C)CC)(C)C.Cl>CO.CN(C)C=O>[OH2:31].[ClH:1].[ClH:1].[NH:12]1[C:16]2=[N:17][CH:18]=[CH:19][C:20]([NH:21][C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([CH2:29][NH:30][C:7]([NH2:8])=[NH:2])=[CH:25][CH:24]=3)=[C:15]2[CH:14]=[N:13]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 22120548HCID 22120548, compound

Product 1

HCID 178478809HCID 178478809, compoundYield 105.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Pyrazole-1-carboxamidine hydrochloride (284 mg) was added to a mixed solution of N-(1H-pyrazolo[3,4-b]pyridin-4-yl)-4-aminomethylbenzamide dihydrochloride (330 mg) and diisopropylethylamine (500 mg) in methanol (5 ml)-dimethylformamide (5 ml), and the mixture was stirred in a stream of nitrogen at room temperature for 8 hours. After the reaction, the reaction mixture was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=3:1) to give white crystals. The crystals were converted to hydrochloride thereof with 15% hydrochloric acid-methanol, and the hydrochloride was recrystallized from methanol-ether to give 205 mg of N-(1H-pyrazolo[3,4-b]pyridin-4-yl)-4-guanidinomethylbenzamide dihydrochloride monohydrate having a melting point of 250-254° C. (dec.)

Workup

  1. customAfter the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=3:1)
  4. customto give white crystals
  5. customwith 15% hydrochloric acid-methanol, and the hydrochloride was recrystallized from methanol-ether

Sources & evidence

ORD record
ord-ad362b44d01044d183fa31efb9c7ca16
Source dataset
uspto-grants-1999_09
Patent number
US05958944

Reaction notes

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