HCID 58835253, compound → HCID 11855960, compound

HRID 1660914Notes

Reaction equation

COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[CH:10]=[CH:11][C:12]3[C:17]([NH:18][C:19]4[C:24]([C:25]([NH:27][CH3:28])=[O:26])=[CH:23][N:22]=[CH:21][CH:20]=4)=[N:16][C:15]([C:29]4[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=4[F:36])=[N:14][C:13]=3[N:37]=2)=CC=1>FC(F)(F)C(O)=O>[NH2:8][C:9]1[CH:10]=[CH:11][C:12]2[C:17]([NH:18][C:19]3[C:24]([C:25]([NH:27][CH3:28])=[O:26])=[CH:23][N:22]=[CH:21][CH:20]=3)=[N:16][C:15]([C:29]3[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:30]=3[F:36])=[N:14][C:13]=2[N:37]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Using the methods descried in Example 2, the protected amine compound, 4-[7-[Bis-(4-methoxy-benzyl)-amino]-2-(5-chloro-2-fluorophenyl)-pyrido[2,3-d]pyrimidin-4-ylamino]-N-methyl-nicotinamide, was prepared. The two methoxybenzyl protecting groups were then removed as follows. A suspension of 4-[7-[Bis-(4-methoxy-benzyl)-amino]-2-(5-chloro-2-fluoro-phenyl)-pyrido[2,3-d]pyrimidin-4-ylamino]-N-methyl-nicotinamide (1.96 g; 3.14 mmol) in neat trifluoroacetic acid (30 mL) was heated to 40° C. for 30 h. The reaction mixture was evaporated to dryness and purified by silica gel chromatography (dichloromethane/EtOAc gradient 95/5 to 5/95) to afford 4-[7-Amino-2-(5-chloro-2-fluoro-phenyl)-pyrido[2,3-d]pyrimidin-4-ylamino]-N-methyl-nicotinamide (0.78 g).

Workup

customThe two methoxybenzyl protecting groups were then removed
customThe reaction mixture was evaporated to dryness
custompurified by silica gel chromatography (dichloromethane/EtOAc gradient 95/5 to 5/95)

Sources & evidence

ORD record: ord-289f6f69f5764c86a4ec870c8778e5d4
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030318B2

Reaction notes

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