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

HRID 588407노트

반응식

HRID 588407 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-93b3c29396b54e698ae151c0a73edf7e
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227967B2

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