Ammonia → 4-[2-(5-Chloro-2-fluoro-phenyl)-6,6-dimethyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-nicotinamide

HRID 1354312Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:29])=[C:6]([C:8]2[N:13]=[C:12]([NH:14][C:15]3[C:20]([C:21](O)=[O:22])=[CH:19][N:18]=[CH:17][CH:16]=3)[C:11]3[CH2:24][C:25]([CH3:28])([CH3:27])[CH2:26][C:10]=3[N:9]=2)[CH:7]=1.C(N1C=CN=C1)([N:32]1C=CN=C1)=O.N>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:29])=[C:6]([C:8]2[N:13]=[C:12]([NH:14][C:15]3[C:20]([C:21]([NH2:32])=[O:22])=[CH:19][N:18]=[CH:17][CH:16]=3)[C:11]3[CH2:24][C:25]([CH3:27])([CH3:28])[CH2:26][C:10]=3[N:9]=2)[CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of 4-[2-(5-Chloro-2-fluoro-phenyl)-6,6-dimethyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino]-nicotinic acid (25 mg, 60.56 μmol) and Carbonyldiimidazole (20 mg, 121.11 μmol) in dry DMF (3 mL) was heated at 70° C. for 1 h then cooled to r.t. A stream of NH3 gas was passed through the solution for 30 min., giving clean conversion to the amide product. Evaporation of the solution, followed by HPLC purification gave, after lyophilization, the pure amide 62 as the TFA salt (20 mg).

Workup

temperaturethen cooled to r.t

Sources & evidence

ORD record: ord-6ccce21faaf3433a984cc2689c1a5ce9
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223766B2

Reaction notes

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