Isobutyramide → HCID 86717526, compound
Reaction equation
[CH3:1][CH:2]([CH3:6])[C:3]([NH2:5])=O.F[B-](F)(F)F.C([O+](CC)CC)C.N[C:20]1[C:21]([NH:29][C@@H:30]2[CH2:35][O:34][C@@H:33]([CH2:36][OH:37])[CH2:32][CH2:31]2)=[C:22]2[S:28][CH:27]=[CH:26][C:23]2=[N:24][CH:25]=1>C1COCC1.C(O)C.CO>[CH:2]([C:3]1[N:29]([C@@H:30]2[CH2:35][O:34][C@@H:33]([CH2:36][OH:37])[CH2:32][CH2:31]2)[C:21]2=[C:22]3[S:28][CH:27]=[CH:26][C:23]3=[N:24][CH:25]=[C:20]2[N:5]=1)([CH3:6])[CH3:1]Participants
Procedure
A mixture of 2-methylpropanamide (71.4 mg, 0.820 mmol) and triethyloxonium tetrafluoroborate (154 mg, 0.812 mmol) in THF (2 mL) was stirred at room temperature for 2 h. The solvent was removed and the residue dissolved in ethanol (0.5 mL) and added to a suspension of {(2R,5S)-5-[(6-aminothieno[3,2-b]pyridin-7-yl)amino]tetrahydro-2H-pyran-2-yl}methanol (69.2 mg, 0.248 mmol) in ethanol (1.7 mL). The mixture was stirred at 80° C. for 1 h. The reaction mixture was cooled to room temperature, diluted with methanol, and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product. LCMS calculated for C17H22N3O2S (M+H)+: m/z=332.1. Found: 332.1.
Workup
- customThe solvent was removed
- dissolutionthe residue dissolved in ethanol (0.5 mL)
- stirringThe mixture was stirred at 80° C. for 1 h
- temperatureThe reaction mixture was cooled to room temperature
- custompurified with prep-LCMS (XBridge C18 column
- washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min)
Sources & evidence
- ORD record
- ord-6c527d7d6a9645ed989bdcafc9199b7c
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181271B2
Reaction notes
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