Diisopropylethylamine → HCID 178479421, compound

HRID 619268Notes

Reaction equation

HRID 619268 reaction equation
[ClH:1].[N:2]1([C:7]([NH2:9])=[NH:8])[CH:6]=[CH:5][CH:4]=N1.Cl.Cl.[N:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:28])[C:20]2[CH:25]=CC(CN)=[CH:22][CH:21]=2)=[CH:14][CH:13]=1.C(N(C(C)C)CC)(C)C>CO>[OH2:28].[ClH:1].[N:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:28])[C:20]2[CH:21]=[CH:22][C:5]([CH2:6][NH:2][C:7]([NH2:9])=[NH:8])=[CH:4][CH:25]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734672Pyrazole-1-carboxamidine monohydrochlorideHCID 22120601173897-49-9

Product 1

HCID 178479421HCID 178479421, compoundYield 112.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyrazole-1-carboxamidine hydrochloride (540 mg) was added to a solution of N-(4-pyridyl)-4-aminomethylbenzamide dihydrochloride (550 mg) and diisopropylethylamine (950 mg) in methanol (7 ml), and the mixture was stirred in a stream of nitrogen at room temperature for 6 hours. After the reaction, the reaction mixture was concentrated to half under reduced pressure, and ethyl acetate was added to precipitate crystals. The crystals were collected by filtration, and recrystallized from methanol-ethyl acetate to give 333 mg of N-(4-pyridyl)-4-guanidinomethylbenzamide monohydrochloride monohydrate having a melting point of 244-248° C.

Workup

  1. customAfter the reaction
  2. concentrationthe reaction mixture was concentrated to half under reduced pressure, and ethyl acetate
  3. additionwas added
  4. customto precipitate crystals
  5. filtrationThe crystals were collected by filtration
  6. customrecrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-48ab38778dca470eac8a95b03650cb42
Source dataset
uspto-grants-1999_09
Patent number
US05958944

Reaction notes

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