Sodium Hydroxide → 3-{[6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carbonyl]-amino}-isonicotinic acid
Reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[NH:10][C:11]([C:13]1[C:18]([NH:19][C:20]2[CH:21]=[N:22][CH:23]=[N:24][CH:25]=2)=[CH:17][CH:16]=[C:15]([CH:26]2[CH2:28][CH2:27]2)[N:14]=1)=[O:12].[OH-].[Na+]>CO.O>[CH:26]1([C:15]2[N:14]=[C:13]([C:11]([NH:10][C:5]3[CH:6]=[N:7][CH:8]=[CH:9][C:4]=3[C:3]([OH:29])=[O:2])=[O:12])[C:18]([NH:19][C:20]3[CH:25]=[N:24][CH:23]=[N:22][CH:21]=3)=[CH:17][CH:16]=2)[CH2:28][CH2:27]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To stirred suspension of 3-{[6-cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carbonyl]-amino}-isonicotinic acid methyl ester (330 mg, 0.84 mmol) in MeOH (5 ml) was added a solution of NaOH (84.5 mg, 2.1 mmol) in water (2 ml) at 0-5° C. After the addition the reaction mixture was stirred at rt for 8 hrs. The solvent was removed in vacuo, the residue was dissolved in water (7 ml), and was washed with EtOAc (2×10 ml). The aqueous layer was then acidified with 1N HCl (pH˜2), and concentrated to obtain the title compound (containing NaCl) as a yellowish sticky solid which was directly used as such for the next step without any further purification.
Workup
- additionAfter the addition the reaction mixture
- stirringwas stirred at rt for 8 hrs
- customThe solvent was removed in vacuo
- dissolutionthe residue was dissolved in water (7 ml)
- washwas washed with EtOAc (2×10 ml)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-99ae6c196a71488889b192086f073d77
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08623866B2
Reaction notes
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