Water → HCID 59520479, compound
Reaction equation
[OH:1][CH2:2][C:3]1[C:4]([C:24]([F:27])([F:26])[F:25])=[N:5][N:6]([CH2:8][C:9]([NH:11][C:12]2[S:16][C:15]3[CH2:17][CH2:18][CH2:19][CH2:20][C:14]=3[C:13]=2[C:21]([NH2:23])=[O:22])=[O:10])[CH:7]=1.[H-].[Na+].I[CH2:31][CH3:32].O>CN(C=O)C>[CH2:31]([O:1][CH2:2][C:3]1[C:4]([C:24]([F:26])([F:25])[F:27])=[N:5][N:6]([CH2:8][C:9]([NH:11][C:12]2[S:16][C:15]3[CH2:17][CH2:18][CH2:19][CH2:20][C:14]=3[C:13]=2[C:21]([NH2:23])=[O:22])=[O:10])[CH:7]=1)[CH3:32]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a solution of 2-(2-(4-(hydroxymethyl)-3-(trifluoromethyl)pyrazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (20 mg, 0.05 mmol) in DMF (2 mL) was added NaH (7 mg, 0.29 mmol) under an atmosphere of N2. The reaction mixture was stirred at RT for 30 min before addition of iodoethane (20 mg, 0.13 mmol). The reaction mixture was heated at 65° C. for 3 h then left to stand at RT overnight. Water (2 mL) was added and the reaction mixture extracted with EtOAc (3×5 mL). The combined EtOAc layers were washed with water (3×10 mL), brine (10 mL), dried over MgSO4 and the solvent removed in vacuo. The residue was purified by preparative reverse phase HPLC to give the desired product as a clear gum (6.7 mg, 0.016 mmol, 31%).
Workup
- waitthen left
- extractionthe reaction mixture extracted with EtOAc (3×5 mL)
- washThe combined EtOAc layers were washed with water (3×10 mL), brine (10 mL)
- dry with materialdried over MgSO4
- customthe solvent removed in vacuo
- customThe residue was purified by preparative reverse phase HPLC
Sources & evidence
- ORD record
- ord-01e41605cc9846ce8933d2e1bb2db48f
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820707B2
Reaction notes
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