(2R)-2-hydroxypropanamide → HCID 178462241, compound

HRID 711980Notes

Reaction equation

HRID 711980 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][CH2:20][C@H:21]1[CH2:26][CH2:25][C@H:24]([NH:27][C:28]2[C:33]([NH2:34])=[CH:32][N:31]=[C:30]3[CH:35]=[CH:36][S:37][C:29]=23)[CH2:23][CH2:22]1>O1CCCC1.C(O)C>[F:19][CH2:20][C@H:21]1[CH2:22][CH2:23][C@H:24]([N:27]2[C:28]3=[C:29]4[S:37][CH:36]=[CH:35][C:30]4=[N:31][CH:32]=[C:33]3[N:34]=[C:3]2[C@H:2]([OH:1])[CH3:6])[CH2:25][CH2:26]1

Participants

6

Reactant 3

HCID 1530236(2R)-2-hydroxypropanamideHCID 2723982Triethyloxonium tetrafluoroborateHCID 178508003HCID 178508003, compound

Product 1

HCID 178462241HCID 178462241, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2R)-2-hydroxypropanamide (0.184 g, 2.07 mmol) and triethyloxonium tetrafluoroborate (0.371 g, 1.95 mmol) in tetrahydrofuran (2.8 mL) was stirred at room temperature for 2 h. The solvent was removed and the residue dissolved in ethanol (1.2 mL) and added to a suspension of N7-[trans-4-(fluoromethyl)cyclohexyl]thieno[3,2-b]pyridine-6,7-diamine (0.18 g, 0.64 mmol) in ethanol (4.3 mL). The resulting 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 (0.10 g, 50%). LCMS calculated for C17H21FN3OS (M+H)+: m/z=334.1. Found: 334.1.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue dissolved in ethanol (1.2 mL)
  3. stirringThe resulting mixture was stirred at 80° C. for 1 h
  4. customThe solvent was removed
  5. customthe residue was purified on RP-HPLC (XBridge C18 column
  6. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-3fbf8588b6694714bad1a2405d86a301
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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