1,2-Dichloroethane → 2-(Tetrahydro-pyran-2-yloxycarbamoyl)-benzo[b]thiophene-5-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[S:9][C:10]([C:12]([OH:14])=O)=[CH:11][C:7]=2[CH:6]=1)=[O:4].[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1NO.C(Cl)CCl.C1C=CC2[N:37]([OH:38])N=NC=2C=1.CCN(C(C)C)C(C)C>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[S:9][C:10]([C:12](=[O:14])[NH:37][O:38][CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][O:17]3)=[CH:11][C:7]=2[CH:6]=1)=[O:4]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of benzo[b]thiophene-2,5-dicarboxylic acid 5-methyl ester (191.3 mg, 0.81 mmol), O -(Tetrahydro-pyran-2-yl)-hydroxylamine (93 mg, 0.79 mmol), EDC (231 mg, 1.20 mmol), HOBt (107 mg, 0.79 mmol) and DIEA (0.30 mL, 2.2 mmol) in anhydrous THF (8 mL) was allowed to stir at rt for three days and then concentrated. To the residue was added MeOH (1 mL) and water (10 mL) and Et2O (5 mL). After stirring for 2 h, the solid formed was washed with water (2×3 mL) and Et2O (5 mL), and dried to give 2-(tetrahydro-pyran-2-yloxycarbamoyl)-benzo[b]thiophene-5-carboxylic acid methyl ester as a pale solid). MS (EI): cal'd 252.0 (M−THP+H+), exp 252.1 (M−THP+H+).
Workup
- concentrationconcentrated
- additionTo the residue was added MeOH (1 mL) and water (10 mL) and Et2O (5 mL)
- stirringAfter stirring for 2 h
- customthe solid formed
- washwas washed with water (2×3 mL) and Et2O (5 mL)
- customdried
Sources & evidence
- ORD record
- ord-6316083be0f54d14bc2a5da98ae2cce2
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935724B2
Reaction notes
Loading…