Sodium Hydroxide → HCID 58835252, compound

HRID 1660912Notes

Reaction equation

HRID 1660912 reaction equation
C[O:2][C:3](=[O:35])[C:4]1[C:9]([NH:10][C:11]2[C:12]3[CH:28]=[CH:27][C:26]([NH:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])=[N:25][C:13]=3[N:14]=[C:15]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=3[F:24])[N:16]=2)=[CH:8][CH:7]=[N:6][CH:5]=1.[OH-].[Na+]>CO>[Cl:23][C:21]1[CH:20]=[CH:19][C:18]([F:24])=[C:17]([C:15]2[N:16]=[C:11]([NH:10][C:9]3[C:4]([C:3]([OH:35])=[O:2])=[CH:5][N:6]=[CH:7][CH:8]=3)[C:12]3[CH:28]=[CH:27][C:26]([NH:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])=[N:25][C:13]=3[N:14]=2)[CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58835245HCID 58835245, compound

Product 1

HCID 58835252HCID 58835252, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of the ester, 4-[2-(5-Chloro-2-fluoro-phenyl)-7-(2-dimethylamino-ethylamino)-pyrido[2,3-d]pyrimidin-4-ylamino]-nicotinic acid methyl ester (0.300 g) in MeOH (20 ml) was added a 1N NaOH (aq) (1.0 ml) and the reaction mixture was heated to reflux for 2 h. The solution was cooled to rt and concentrated in vacuo. Water (50 ml) was added to the crude material and the aqueous layer was acidified with HCl (1 N) and the mixture was placed in the freezer. The solid was filtered, washed with water and dried to give 4-[2-(5-Chloro-2-fluorophenyl)-7-(2-dimethylamino-ethylamino)-pyrido[2,3-d]pyrimidin-4-ylamino]-nicotinic acid as a cream colored solid. This material was used without further purification.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. concentrationconcentrated in vacuo
  4. additionWater (50 ml) was added to the crude material
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-646e877f299b419ba1b4b111294c29b5
Source dataset
uspto-grants-2011_10
Patent number
US08030318B2

Reaction notes

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