(2R)-2-hydroxypropanamide → HCID 178462250, compound

HRID 711954Notes

Reaction equation

HRID 711954 reaction equation
[OH:1][C@H:2]([CH3:6])[C:3](N)=O.F[B-](F)(F)F.C([O+](CC)CC)C.[N:19]1([C@@H:24]2[CH2:29][CH2:28][C@H:27]([NH:30][C:31]3[C:36]([NH2:37])=[CH:35][N:34]=[C:33]4[CH:38]=[CH:39][S:40][C:32]=34)[CH2:26][CH2:25]2)[CH:23]=[N:22][CH:21]=[N:20]1>O1CCCC1.C(O)C>[N:19]1([C@@H:24]2[CH2:29][CH2:28][C@H:27]([N:30]3[C:31]4=[C:32]5[S:40][CH:39]=[CH:38][C:33]5=[N:34][CH:35]=[C:36]4[N:37]=[C:3]3[C@H:2]([OH:1])[CH3:6])[CH2:26][CH2:25]2)[CH:23]=[N:22][CH:21]=[N:20]1

Participants

6

Reactant 3

HCID 1530236(2R)-2-hydroxypropanamideHCID 2723982Triethyloxonium tetrafluoroborateHCID 178508005HCID 178508005, compound

Product 1

HCID 178462250HCID 178462250, compoundYield 5.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2R)-2-hydroxypropanamide (28 mg, 0.32 mmol) and triethyloxonium tetrafluoroborate (60 mg, 0.32 mmol) in tetrahydrofuran (0.4 mL) became a solution after stirring for 15 min. After another 45 min, this solution was added to a mixture of N7-[cis-4-(1H-1,2,4-triazol-1-yl)cyclohexyl]thieno[3,2-b]pyridine-6,7-diamine (25 mg, 0.080 mmol) in ethanol (0.8 mL) and heated at reflux overnight. 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 (1.7 mg, 5.8%). LCMS calculated for C18H21N6OS (M+H)+: m/z=369.1. Found: 369.1.

Workup

  1. waitAfter another 45 min
  2. temperatureheated
  3. temperatureat reflux overnight
  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-35613756ae584674bc13aaf545e1de4e
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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