Carbonic acid-guanidine (1:1) → HCID 178509681, compound

HRID 479568Notes

Reaction equation

C(=O)(O)O.[NH2:5][C:6]([NH2:8])=[NH:7].Cl[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]#[N:27])[CH:21]=3)[CH:18]=2)[C:13]([Cl:28])=[CH:12][N:11]=1>CN1C(=O)CCC1>[Cl:28][C:13]1[C:14]2[C:19](=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]#[N:27])[CH:21]=3)=[CH:16][CH:15]=2)[C:10]([NH:7][C:6]([NH2:8])=[NH:5])=[N:11][CH:12]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A stirred suspension of guanidine carbonate (720 g, 4.0 mol) in NMP (5 L) was heated to 130° C. under N2 for 1 hour. The suspension was cooled to room temperature and 1,4-dichloro-7-(3-cyanophenyl)isoquinoline (1.0 kg, 3.3 mmol) was added as a solid. The mixture was heated at 130° C. for 4 hours, cooled to room temperature, filtered through a pad of clarcel. Water (6.7 L) was added to the filtrate. The resultant slurry was cooled to 5° C., stirred for 1 hour and the solid collected by filtration. The solid was washed with a mixture of NMP:water (1:1, 4 L) and water (4 L) and dried in vacuo at 50° C. to give (4-chloro-7-(3-cyanophenyl)isoquinolin-1-yl)guanidine (900 g, 2.8 mol, 85%) as a green solid.

Workup

temperatureThe suspension was cooled to room temperature
temperatureThe mixture was heated at 130° C. for 4 hours
temperaturecooled to room temperature
filtrationfiltered through a pad of clarcel
additionWater (6.7 L) was added to the filtrate
temperatureThe resultant slurry was cooled to 5° C.
filtrationthe solid collected by filtration
washThe solid was washed with a mixture of NMP:water (1:1, 4 L) and water (4 L)
customdried in vacuo at 50° C.

Sources & evidence

ORD record: ord-f5b5157341f0481c93f0a0fb999e25e6
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06645979B2

Reaction notes

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