Cyclopropanecarboxamide → HCID 86717527, compound

HRID 712068Notes

Reaction equation

HRID 712068 reaction equation
[CH:1]1([C:4](N)=O)[CH2:3][CH2:2]1.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][O: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>C1COCC1.C(O)C.CO>[CH:1]1([C:4]2[N:29]([C@@H:30]3[CH2:35][O:34][C@@H:33]([CH2:36][OH:37])[CH2:32][CH2:31]3)[C:21]3=[C:22]4[S:28][CH:27]=[CH:26][C:23]4=[N:24][CH:25]=[C:20]3[N:19]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 80376CyclopropanecarboxamideHCID 2723982Triethyloxonium tetrafluoroborateHCID 86717520HCID 86717520, compound

Product 1

HCID 86717527HCID 86717527, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of cyclopropanecarboxamide (72.6 mg, 0.853 mmol) and triethyloxonium tetrafluoroborate (0.161 g, 0.845 mmol) in THF (2 mL) was stirred at room temperature for 2 h. The solvent was removed and the residue dissolved in ethanol (0.48 mL) and added to a suspension of {(2R,5S)-5-[(6-aminothieno[3,2-b]pyridin-7-yl)amino]tetrahydro-2H-pyran-2-yl}methanol (72.0 mg, 0.258 mmol) in ethanol (1.8 mL). The mixture was stirred at 80° C. for 1 h. The reaction mixture was cooled to room temperature, diluted with methanol, and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product. LCMS calculated for C17H20N3O2S (M+H)+: m/z=330.1. Found: 330.0.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue dissolved in ethanol (0.48 mL)
  3. stirringThe mixture was stirred at 80° C. for 1 h
  4. temperatureThe reaction mixture was cooled to room temperature
  5. custompurified with prep-LCMS (XBridge C18 column
  6. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-1ec22a54ac914d96a87e05f9e97716bc
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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