(2R)-2-hydroxypropanamide → HCID 178462240, compound

HRID 711948Notes

Reaction equation

HRID 711948 reaction equation
[OH:1][C@H:2]([CH3:6])[C:3](N)=O.F[B-](F)(F)F.C([O+](CC)CC)C.[CH3:19][S:20]([CH2:23][CH2:24][C@H:25]1[CH2:30][CH2:29][C@H:28]([NH:31][C:32]2[C:37]([NH2:38])=[CH:36][N:35]=[C:34]3[CH:39]=[CH:40][S:41][C:33]=23)[CH2:27][CH2:26]1)(=[O:22])=[O:21]>O1CCCC1.C(O)C>[CH3:19][S:20]([CH2:23][CH2:24][C@H:25]1[CH2:30][CH2:29][C@H:28]([N:31]2[C:32]3=[C:33]4[S:41][CH:40]=[CH:39][C:34]4=[N:35][CH:36]=[C:37]3[N:38]=[C:3]2[C@H:2]([OH:1])[CH3:6])[CH2:27][CH2:26]1)(=[O:21])=[O:22]

Participants

6

Reactant 3

HCID 1530236(2R)-2-hydroxypropanamideHCID 2723982Triethyloxonium tetrafluoroborateHCID 178504876HCID 178504876, compound

Product 1

HCID 178462240HCID 178462240, compoundYield 1.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2R)-2-hydroxypropanamide (52 mg, 0.59 mmol) and triethyloxonium tetrafluoroborate (0.11 g, 0.59 mmol) in tetrahydrofuran (1 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-(methylsulfonyl)ethyl]cyclohexyl}thieno[3,2-b]pyridine-6,7-diamine (83 mg, 0.23 mmol) in ethanol (2 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 (1.1 mg, 1.1%). LCMS calculated for C19H26N3O3S2 (M±H)+: m/z=408.1. Found: 408.1.

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-08ccaa2a5a40457d90ce2c41616a7b01
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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