Sodium Hydroxide → HCID 59599436, compound
Reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH2:13][CH:14]3[CH2:16][CH:15]3[C:17]([O:19]CC)=[O:18])[CH:12]=2)=[CH:4][C:3]=1[O:22][CH:23]([C:25]1[C:30]([Cl:31])=[CH:29][CH:28]=[C:27]([F:32])[C:26]=1[Cl:33])[CH3:24].[OH-].[Na+]>CO>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH2:13][CH:14]3[CH2:16][CH:15]3[C:17]([OH:19])=[O:18])[CH:12]=2)=[CH:4][C:3]=1[O:22][CH:23]([C:25]1[C:30]([Cl:31])=[CH:29][CH:28]=[C:27]([F:32])[C:26]=1[Cl:33])[CH3:24]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a reaction solution of compound (4-6) (377 mg, 0.76 mmol) in 5.0 mL of MeOH at room temperature under N2 was added another solution of 2.0 N NaOH (2) (1.5 mL, 3.04 mmol). The resulting mixture was stirred at 80° C. for 3 hours. The reaction mixture was concentrated by vacuum to remove most of the MeOH and acidified by 2 M HCl to pH 4.0. The mixture was extracted with CH2Cl2 (2×200 mL); the organic layers were washed with brine (50 mL), and dried (Na2SO4) and concentrated by vacuum to give 324 mg of (4-7) as a yellow solid. (92% yield). 1H NMR (400 MHz, DMSO-D6) δ ppm 0.92-1.04 (m, 2H) 1.57-1.72 (m, 2H) 1.76-1.90 (m, 3H) 3.98-4.18 (m, 2H) 6.46 (s, 2H) 6.89-7.02 (m, 1H) 7.29-7.52 (m, 2H) 7.52-7.63 (m, 2H) 7.73 (d, J=1.52 Hz, 1H) 7.94 (s, 1H) 12.19 (s, 1H). LCMS calcd for C21H19Cl2FN4O3(M−H) 463, found 463. HPLC purity 87%.
Workup
- concentrationThe reaction mixture was concentrated by vacuum
- customto remove most of the MeOH
- extractionThe mixture was extracted with CH2Cl2 (2×200 mL)
- washthe organic layers were washed with brine (50 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated by vacuum
Sources & evidence
- ORD record
- ord-860ac981e2174ef896689009c0c47a2c
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07858643B2
Reaction notes
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