Acetic Acid → HCID 178476691, compound

HRID 479569Notes

Reaction equation

HRID 479569 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[Cl:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]#[N:23])[CH:17]=3)=[CH:13][CH:14]=2)[C:9]([NH:24][C:25]([NH2:27])=[NH:26])=[N:8][CH:7]=1>COCCOC.CN1C(=O)CCC1>[C:1]([O-:4])(=[O:3])[CH3:2].[Cl:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]#[N:23])[CH:17]=3)=[CH:13][CH:14]=2)[C:9]([NH:24][C:25]([NH2:27])=[NH2+:26])=[N:8][CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 178509681HCID 178509681, compound

Product 1

HCID 178476691HCID 178476691, compoundYield 143%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of acetic acid (0.72 kg, mol) in DME (13.6 L) was added dropwise to a stirred solution of (4-chloro-7-(3-cyanophenyl)isoquinolin-1-yl)guanidine (4.4 kg, 13.7 mol) in NMP (14 kg) at 100° C. After addition the thick slurry was allowed to cool and was stirred overnight at room temperature. The solid was collected by filtration, washed with DME (4.9 L) and dried overnight in vacuo at 50° C. to give (4-chloro-7-(3-cyanophenyl)isoquinolin-1-yl)guanidinium acetate (6 kg, 143%) as an NMP wet off white solid.

Workup

  1. additionAfter addition the thick slurry
  2. temperatureto cool
  3. filtrationThe solid was collected by filtration
  4. washwashed with DME (4.9 L)
  5. customdried overnight in vacuo at 50° C.

Sources & evidence

ORD record
ord-ae65cef656d145368ff3a02a1bf37d59
Source dataset
uspto-grants-2003_11
Patent number
US06645979B2

Reaction notes

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