Methanol → (5-(4-(4-(7-Methoxy-1,5-naphthyridin-4-yloxy)phenylamino)phthalazin-1-yl)thiophen-3-yl)methanol
Reaction equation
C([O:4][CH2:5][C:6]1[CH:10]=[C:9]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]4[C:38]5[C:33](=[CH:34][C:35]([O:39][CH3:40])=[CH:36][N:37]=5)[N:32]=[CH:31][CH:30]=4)=[CH:24][CH:23]=3)=[N:13][N:12]=2)[S:8][CH:7]=1)(=O)C.C1COCC1.CO.[OH-].[Li+]>O>[CH3:40][O:39][C:35]1[CH:34]=[C:33]2[C:38]([C:29]([O:28][C:25]3[CH:26]=[CH:27][C:22]([NH:21][C:14]4[C:15]5[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=5)[C:11]([C:9]5[S:8][CH:7]=[C:6]([CH2:5][OH:4])[CH:10]=5)=[N:12][N:13]=4)=[CH:23][CH:24]=3)=[CH:30][CH:31]=[N:32]2)=[N:37][CH:36]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A scintillation vial was charged with (5-(4-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenylamino)phthalazin-1-yl)thiophen-3-yl)methyl acetate (137 mg, 249 μmol), 1.0 mL 3:1:1 THF:MeOH:water and lithium hydroxide (47.8 mg, 1994 μmol). The homogeneous mixture was stirred at RT for 2 h. Water was added to the mixture, and the precipitated solids were filtered, washed with water, and dried. The crude solids were purified by reverse phase chromatography, Gilson, 10-90% 0.1% TFA/ACN in water to provide (5-(4-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenylamino)phthalazin-1-yl)thiophen-3-yl)methanol. MS: [M+H]=508.
Workup
- filtrationthe precipitated solids were filtered
- washwashed with water
- customdried
- customThe crude solids were purified by reverse phase chromatography, Gilson, 10-90% 0.1% TFA/ACN in water
Sources & evidence
- ORD record
- ord-bfc682bf529e495f879fe163fa9c1894
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776857B2
Reaction notes
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