Methanamine, N-methoxy-, hydrochloride (1:1) → 3-(4-chlorobenzyl)-3-formamido-N-methoxy-N-methylcyclobutanecarboxamide

HRID 1778597노트

반응식

HRID 1778597 반응식
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][C:7]2([NH:14][CH:15]=[O:16])[CH2:10][CH:9]([C:11]([OH:13])=O)[CH2:8]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Cl.[CH3:29][O:30][NH:31][CH3:32].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2([NH:14][CH:15]=[O:16])[CH2:8][CH:9]([C:11]([N:31]([O:30][CH3:29])[CH3:32])=[O:13])[CH2:10]2)=[CH:17][CH:18]=1

참가 물질

6

반응물 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 895142413-(4-Chlorobenzyl)-3-formamidocyclobutanecarboxylic acid

생성물 1

HCID 895144553-(4-chlorobenzyl)-3-formamido-N-methoxy-N-methylcyclobutanecarboxamide수율 33.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 3-(4-chlorobenzyl)-3-formamidocyclobutanecarboxylic acid (1.3 g, 4.87 mmol), DIPEA (2.17 mL, 12.6 mmol), O,N-dimethylhydroxylamine hydrochloride (617 mg, 6.33 mmol) in dichloromethane (20 mL) was treated with HATU (2.2 g, 5.84 mmol) and stirred at room temperature for 16 h. The solution was diluted with dichloromethane (20 mL), washed successively with 1 M HCl (2×), 5% aqueous NaHCO3 and saturated aqueous sodium chloride, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (gradient 0.5-1.0% methanol in dichloromethane) to give the subject compound (0.5 g, 33.3%). ESI MS found for C15H19ClN2O3 m/z [211.4 (M+1), 233.4 (M+Na+)].

후처리

  1. washwashed successively with 1 M HCl (2×), 5% aqueous NaHCO3 and saturated aqueous sodium chloride
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (gradient 0.5-1.0% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-185232224a2a474ab3a89fcf72b289a3
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266908B2

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