Dimethylformamide → 4-((2-(5-Chloro-2-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)amino)-N-methylnicotinamide

HRID 1660913Notes

Reaction equation

HRID 1660913 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:34])=[C:6]([C:8]2[N:9]=[C:10]([NH:24][C:25]3[C:30](C(O)=O)=[CH:29][N:28]=[CH:27][CH:26]=3)[C:11]3[CH:17]=[CH:16][C:15](NCCN(C)C)=N[C:12]=3[N:13]=2)[CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.CN.[CH3:49][N:50]([CH:52]=[O:53])C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:34])=[C:6]([C:8]2[N:9]=[C:10]([NH:24][C:25]3[C:30]([C:52]([NH:50][CH3:49])=[O:53])=[CH:29][N:28]=[CH:27][CH:26]=3)[C:11]3[CH2:17][CH2:16][CH2:15][C:12]=3[N:13]=2)[CH:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 58835252HCID 58835252, compound

Product 1

HCID 98009714-((2-(5-Chloro-2-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)amino)-N-methylnicotinamideYield 68%

Procedure

To a suspension of substituted nicotinic acid, 4-[2-(5-Chloro-2-fluoro-phenyl)-7-(2-dimethylamino-ethylamino)-pyrido[2,3-d]pyrimidin-4-ylamino]-nicotinic acid (0.030 g) in dry DMF (1 ml) was added Carbonyldiimidazole (0.020 g) followed by methylamine (156 uL, 2 M solution if THF). The reaction mixture was stirred at room temperature for 16 h. The crude residue was purified by preparative HPLC (Acetonitrile/water 5% to 95% gradient) to give 4-[2-(5-Chloro-2-fluoro-phenyl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-N-methyl-nicotinamide (280 mg, 68%) as a white solid.

Workup

  1. customThe crude residue was purified by preparative HPLC (Acetonitrile/water 5% to 95% gradient)

Sources & evidence

ORD record
ord-79ede5ff2fe54be19a6e2b37db3f36fe
Source dataset
uspto-grants-2011_10
Patent number
US08030318B2

Reaction notes

Loading…