Methylamine → HCID 11855959, compound

HRID 1660915Notes

Reaction equation

[C:1](N1C=CN=C1)([N:3]1C=CN=C1)=O.[Cl:13][C:14]1[CH:15]=[CH:16][C:17](F)=[C:18]([C:20]2[N:21]=[C:22]([NH:30][C:31]3[C:36]([C:37](O)=[O:38])=[CH:35][N:34]=[CH:33][CH:32]=3)[C:23]3[CH:29]=[CH:28][CH:27]=[N:26][C:24]=3[N:25]=2)[CH:19]=1.[CH3:41][NH2:42]>CN(C=O)C>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([NH:42][CH3:41])=[C:18]([C:20]2[N:21]=[C:22]([NH:30][C:31]3[C:36]([C:37]([NH:3][CH3:1])=[O:38])=[CH:35][N:34]=[CH:33][CH:32]=3)[C:23]3[CH:29]=[CH:28][CH:27]=[N:26][C:24]=3[N:25]=2)[CH:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Carbonyldiimidazole (180 mg, 1.11 mmol) was added to a stirred suspension of the acid, 4-[2-(5-Chloro-2-fluoro-phenyl)-pyrido[2,3-d]pyrimidin-4-ylamino]-nicotinic acid (240 mg, 0.56 mmol) in dry DMF (15 ml). The reaction was heated to 60° C. for 2 hours under nitrogen. The reaction was cooled to room temperature and MeNH2 (2M in THF, 5 equivalents) was added and the reaction stirred for 18 hours. The reaction mixture was partitioned between CHCl3 (50 mL) and water (50 mL). The organic layer was further washed with water (3×50 mL). The product precipitated out of the CHCl3 solution and was filter to give compound 4-[2-(5-Chloro-2-methylamino-phenyl)-pyrido[2,3-d]pyrimidin-4-ylamino]-N-methyl-nicotinamide (47 mg, 19% yield).

Workup

temperatureThe reaction was cooled to room temperature
customThe reaction mixture was partitioned between CHCl3 (50 mL) and water (50 mL)
washThe organic layer was further washed with water (3×50 mL)
customThe product precipitated out of the CHCl3 solution
filtrationwas filter

Sources & evidence

ORD record: ord-e6b9e0784f2a474e96c7887a0cc6572b
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030318B2

Reaction notes

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