Potassium Carbonate → N-{[3-amino-1-(6-amino-5-cyanopyrimidin-4-yl)pyrrolidin-3-yl]methyl}-2,4-difluorobenzamide

HRID 632731Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.Cl.Cl.[NH2:13][C:14]1([CH2:19][NH:20][C:21](=[O:30])[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[F:29])[CH2:18][CH2:17][NH:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[NH2:13][C:14]1([CH2:19][NH:20][C:21](=[O:30])[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=2[F:29])[CH2:18][CH2:17][N:16]([C:6]2[C:7]([C:8]#[N:9])=[C:2]([NH2:1])[N:3]=[CH:4][N:5]=2)[CH2:15]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-amino-6-chloropyrimidine-5-carbonitrile (72.0 mg; 0.47 mmol; 1.02 eq.), N-[(3-aminopyrrolidin-3-yl)methyl]-2,4-difluorobenzamide dihydrochloride (150.0 mg; 0.46 mmol; 1.0 eq.), potassium carbonate (126.3 mg; 0.91 mmol; 2.0 eq.) in DMSO (2.00 ml) was stirred at 60° C. for 2 h. The reaction mixture was workup and the crude was purified by reverse phase pre-HPLC (Waters, acetonitrile/0.1% NH4OH in water) to afford the title compound in 70% yield. LC-MS: (M+1=374, obsd.=374).

Workup

customthe crude was purified by reverse phase pre-HPLC (Waters, acetonitrile/0.1% NH4OH in water)

Sources & evidence

ORD record: ord-443cf14492d04b90aceb58509083dc58
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321760B2

Reaction notes

Loading…