Methanamine, N-methoxy-, hydrochloride (1:1) → 3-Furancarboxamide,tetrahydro-N-methoxy-N-methyl-(9CI)

HRID 588407Notes

Reaction equation

HRID 588407 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=O)[CH2:2]1.CN([C:12]([O:16][N:17]1N=NC2C=CC=C[C:18]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CNOC.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:12][O:16][N:17]([CH3:18])[C:6]([CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)=[O:8]

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 4661317(R)-Tetrahydro-3-furoic acid

Product 1

HCID 450845223-Furancarboxamide,tetrahydro-N-methoxy-N-methyl-(9CI)Yield 161.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Tetrahydro-3-furoic acid (412 μL, 4.31 mmol) was dissolved in DMF (18 mL) and HBTU (1.96 g, 5.17 mmol) was added. The reaction mixture was stirred for 1 h and N,O-dimethylhydroxylamine hydrochloride (504 mg, 5.17 mmol) and DIPEA (2.25 mL, 12.9 mmol) were added. The reaction mixture was stirred overnight and concentrated in vacuo. The residue was diluted with DCM (40 mL) and washed with sat aq NH4Cl (20 mL) and sat aq Na2CO3 (20 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by normal phase column chromatography to give the crude title compound as a yellow gum (1.11 g). LCMS (ES+): 160.1 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with DCM (40 mL)
  4. washwashed
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by normal phase column chromatography

Sources & evidence

ORD record
ord-93b3c29396b54e698ae151c0a73edf7e
Source dataset
uspto-grants-2016_01
Patent number
US09227967B2

Reaction notes

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