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

HRID 1778597ノート

反応式

HRID 1778597 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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+)].

後処理

  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)

出典と根拠

ORDレコード
ord-185232224a2a474ab3a89fcf72b289a3
出典データセット
uspto-grants-2016_02
特許番号
US09266908B2

反応ノート

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