(2R)-2-hydroxypropanamide → HCID 73776351, compound
Reaction equation
[OH:1][C@H:2]([CH3:6])[C:3](N)=O.F[B-](F)(F)F.C([O+](CC)CC)C.[CH:19]1([NH:25][C:26]2[C:31]([NH2:32])=[CH:30][N:29]=[C:28]3[CH:33]=[CH:34][S:35][C:27]=23)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>O1CCCC1.C(O)C>[CH:19]1([N:25]2[C:26]3=[C:27]4[S:35][CH:34]=[CH:33][C:28]4=[N:29][CH:30]=[C:31]3[N:32]=[C:3]2[C@H:2]([OH:1])[CH3:6])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1Participants
6
Procedure
A mixture of (2R)-2-hydroxypropanamide (49 mg, 0.55 mmol) and triethyloxonium tetrafluoroborate (98 mg, 0.51 mmol) in tetrahydrofuran (0.75 mL) was stirred at room temperature for 2 h. The solvent was removed and the residue dissolved in ethanol (0.32 mL) and added to a suspension of N7-cyclohexylthieno[3,2-b]pyridine-6,7-diamine (42 mg, 0.17 mmol) in ethanol (1.1 mL). The reaction mixture was stirred at 80° C. for 1 h. The solvent was removed, and the residue was purified on RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min) to give the desired product (1 mg, 2%). LCMS calculated for C16H20N3OS (M+H)+: m/z=302.1. Found: 302.1.
Workup
- customThe solvent was removed
- dissolutionthe residue dissolved in ethanol (0.32 mL)
- stirringThe reaction mixture was stirred at 80° C. for 1 h
- customThe solvent was removed
- customthe residue was purified on RP-HPLC (XBridge C18 column
- washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)
Sources & evidence
- ORD record
- ord-b63666a964be4208a07b9c70ecbabb58
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181271B2
Reaction notes
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