(2R)-2-hydroxypropanamide → HCID 86717556, compound

HRID 712102Notes

Reaction equation

HRID 712102 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][C@@H:34]([NH:36][C:37](=[O:46])[O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@@H:33]([CH2:47][C:48]#[N:49])[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>[C:48]([CH2:47][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][C@H:34]1[NH:36][C:37](=[O:46])[O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)#[N:49]

Participants

6

Reactant 3

HCID 1530236(2R)-2-hydroxypropanamideHCID 2723982Triethyloxonium tetrafluoroborateHCID 86717555HCID 86717555, compound

Product 1

HCID 86717556HCID 86717556, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2R)-2-hydroxypropanamide (17.1 mg, 0.192 mmol) and triethyloxonium tetrafluoroborate (34.2 mg, 0.180 mmol) in tetrahydrofuran (0.36 mL) was stirred at room temperature for 75 min and then concentrated. The residue was dissolved in ethanol (0.14 mL), and this solution was then added to a solution of benzyl [(1R,2R,5S)-5-[(6-aminothieno[3,2-b]pyridin-7-yl)amino]-2-(cyanomethyl)cyclohexyl]carbamate (26 mg, 0.060 mmol) in ethanol (0.36 mL) in a vial. The resulting mixture was stirred at 80° C. overnight. After cooling, the mixture was concentrated and purified on silica gel, eluted with 0-10% MeOH in dichloromethane to give 18 mg of the desired product. LCMS calculated for C26H28N5O3S (M+H)+: m/z=490.2. Found: 490.0.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethanol (0.14 mL)
  3. stirringThe resulting mixture was stirred at 80° C. overnight
  4. temperatureAfter cooling
  5. concentrationthe mixture was concentrated
  6. custompurified on silica gel
  7. washeluted with 0-10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-1270c9a921da49d68d4f25f1c384d2cf
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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