Benzoic Acid → HCID 178509682, compound

HRID 479570Notes

Reaction equation

HRID 479570 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#[N:28])[CH:22]=3)=[CH:18][CH:19]=2)[C:14]([NH:29][C:30]([NH2:32])=[NH:31])=[N:13][CH:12]=1>CC(N(C)C)=O>[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#[N:28])[CH:22]=3)=[CH:18][CH:19]=2)[C:14]([NH:29][C:30]([NH2:32])=[NH2+:31])=[N:13][CH:12]=1

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 178509681HCID 178509681, compound

Product 1

HCID 178509682HCID 178509682, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
40 °C

Procedure

A slurry of benzoic acid (3.95 kg, 32.33 mol) and (4-chloro-7-(3-cyanophenyl)isoquinolin-1-yl)guanidine (10.2 kg, 31.69 mol) in DMA (61.2 L) was heated at 60° C. until dissolution was complete. The solution was slowly cooled to 40° C., seeded, granulated at 40° C. and then at ambient temperature. The thick slurry was cooled to 0° C., granulated, and the solid was collected by filtration, washed with DMA (5.1 L) and MeCN (10.2 L) and dried overnight in vacuo at 55° C to give (4-chloro-7-(3-cyanophenyl)isoquinolin-1-yl)guanidinium benzoate (9.85 kg, 22.19 mol, 70%) as an off white solid.

Workup

  1. customgranulated at 40° C.
  2. customat ambient temperature
  3. temperatureThe thick slurry was cooled to 0° C.
  4. filtrationthe solid was collected by filtration
  5. washwashed with DMA (5.1 L) and MeCN (10.2 L)
  6. customdried overnight in vacuo at 55° C

Sources & evidence

ORD record
ord-7254c3ecca9c4bb58ffbbafa60424035
Source dataset
uspto-grants-2003_11
Patent number
US06645979B2

Reaction notes

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