(2R)-2-hydroxypropanamide → HCID 178462249, compound

HRID 711978Notes

Reaction equation

HRID 711978 reaction equation
[OH:1][C@H:2]([CH3:6])[C:3](N)=O.F[B-](F)(F)F.C([O+](CC)CC)C.[NH2:19][C:20]1[C:21]([NH:29][C@H:30]2[CH2:35][CH2:34][C@H:33]([CH2:36][OH:37])[CH2:32][CH2:31]2)=[C:22]2[S:28][CH:27]=[CH:26][C:23]2=[N:24][CH:25]=1>O1CCCC1.C(O)C>[OH:37][CH2:36][C@H:33]1[CH2:32][CH2:31][C@H:30]([N:29]2[C:21]3=[C:22]4[S:28][CH:27]=[CH:26][C:23]4=[N:24][CH:25]=[C:20]3[N:19]=[C:3]2[C@H:2]([OH:1])[CH3:6])[CH2:35][CH2:34]1

Participants

6

Reactant 3

HCID 1530236(2R)-2-hydroxypropanamideHCID 2723982Triethyloxonium tetrafluoroborateHCID 178508004HCID 178508004, compound

Product 1

HCID 178462249HCID 178462249, compoundYield 4.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2R)-2-hydroxypropanamide (42 mg, 0.48 mmol) and triethyloxonium tetrafluoroborate (85 mg, 0.45 mmol) in tetrahydrofuran (0.65 mL) was stirred at room temperature for 2 h. The solvent was removed, and the residue dissolved in ethanol (0.27 mL) and added to a suspension of {trans-4-[(6-aminothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}methanol (41 mg, 0.15 mmol) in ethanol (0.99 mL). The resulting mixture was stirred at 85° 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 (2.3 mg, 4.7%). LCMS calculated for C17H22N3O2S (M+H)+: m/z=332.1. Found: 332.1.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue dissolved in ethanol (0.27 mL)
  3. stirringThe resulting mixture was stirred at 85° 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-b6fed2bf8e724b55895fe49874379e17
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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