Reaction equation
[OH:1][C@H:2]([CH3:6])[C:3](O)=[O:4].[F:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:22]3[C:17](=[CH:18][C:19]([O:23][C@H:24]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=4)[C@@H:25]([NH2:27])[CH3:26])=[CH:20][CH:21]=3)[CH:16]=[N:15]2)=[CH:10][CH:9]=1>C1COCC1>[F:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[C:22]3[C:17](=[CH:18][C:19]([O:23][C@H:24]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=4)[C@@H:25]([NH:27][C:3](=[O:4])[C@H:2]([OH:1])[CH3:6])[CH3:26])=[CH:20][CH:21]=3)[CH:16]=[N:15]2)=[CH:12][CH:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 1,1-carbonyldiimidazole (31 mg, 190 μmol) in THF (1 ml) was added (2R)-2-hydroxypropanoic acid (18 mg, 20 μmol) to give a colorless solution. The reaction mixture was stirred for 1 h at r.t. Then a solution of (1R,2S)-1-{[1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-(3-methoxyphenyl)propan-2-amine (6a, 39 mg, 100 μmol) in THF (0.5 ml) was added, and the stirring was continued at r.t. overnight. The solvent was removed in vacuo, the residue dissolved in acetonitrile/water mixture, and the crude product purified by preparative HPLC. Yield 16 mg (35%).
Workup
- customto give a colorless solution
- waitthe stirring was continued at r.t. overnight
- customThe solvent was removed in vacuo
- dissolutionthe residue dissolved in acetonitrile/water mixture
- customthe crude product purified by preparative HPLC
Sources & evidence
- ORD record
- ord-c2758e01e78645c98e4dd1402e0daf81
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728030B2
Linked notes
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