(2R)-2-hydroxypropanamide → HCID 178462251, compound

HRID 711942Notes

Reaction equation

HRID 711942 reaction equation
[OH:1][C@H:2]([CH3:6])[C:3](N)=O.F[B-](F)(F)F.C([O+](CC)CC)C.[F:19][C:20]([F:41])([F:40])[CH2:21][NH:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([NH:29][C:30]2[C:35]([NH2:36])=[CH:34][N:33]=[C:32]3[CH:37]=[CH:38][S:39][C:31]=23)[CH2:25][CH2:24]1>O1CCCC1.C(O)C>[F:41][C:20]([F:19])([F:40])[CH2:21][NH:22][C@H:23]1[CH2:24][CH2:25][C@H:26]([N:29]2[C:30]3=[C:31]4[S:39][CH:38]=[CH:37][C:32]4=[N:33][CH:34]=[C:35]3[N:36]=[C:3]2[C@H:2]([OH:1])[CH3:6])[CH2:27][CH2:28]1

Participants

6

Reactant 3

HCID 1530236(2R)-2-hydroxypropanamideHCID 2723982Triethyloxonium tetrafluoroborateHCID 178508006HCID 178508006, compound

Product 1

HCID 178462251HCID 178462251, compoundYield 10.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2R)-2-hydroxypropanamide (21 mg, 0.24 mmol) and triethyloxonium tetrafluoroborate (45 mg, 0.24 mmol) in tetrahydrofuran (0.3 mL) became a solution after stirring for 15 min. After another 45 min, this solution was added to a mixture of N7-{trans-4-[(2,2,2-trifluoroethyl)amino]cyclohexyl}thieno[3,2-b]pyridine-6,7-diamine (27 mg, 0.078 mmol) in ethanol (0.62 mL) and heated at reflux for 2 h. The resulting mixture 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 (3.2 mg, 10%). LCMS calculated for C18H22F3N4OS (M+H)+: m/z=399.1. Found: 399.2.

Workup

  1. waitAfter another 45 min
  2. temperatureheated
  3. temperatureat reflux for 2 h
  4. customThe resulting mixture was purified on RP-HPLC (XBridge C18 column
  5. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-8404f53544054f1ab19f3ed02e804d47
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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