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Cyclopropylamine → N-Cyclopropyl-6-(4-{1-[8-(hydroxymethyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-3-yl]cyclopropyl}phenyl)nicotinamide

HRID 1424106
ノート
印刷プレビュー

反応式

HRID 1424106 の反応式
[OH:1][CH2:2][C:3]1([CH3:31])[S:9][CH2:8][CH2:7][N:6]2[C:10]([C:13]3([C:16]4[CH:21]=[CH:20][C:19]([C:22]5[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][N:23]=5)=[CH:18][CH:17]=4)[CH2:15][CH2:14]3)=[N:11][N:12]=[C:5]2[CH2:4]1.[CH:32]1([NH2:35])[CH2:34][CH2:33]1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH:32]1([NH:35][C:26](=[O:28])[C:25]2[CH:29]=[CH:30][C:22]([C:19]3[CH:18]=[CH:17][C:16]([C:13]4([C:10]5[N:6]6[CH2:7][CH2:8][S:9][C:3]([CH2:2][OH:1])([CH3:31])[CH2:4][C:5]6=[N:12][N:11]=5)[CH2:14][CH2:15]4)=[CH:21][CH:20]=3)=[N:23][CH:24]=2)[CH2:34][CH2:33]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 867129516-(4-{1-[8-(Hydroxymethyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-3-yl]cyclopropyl}phenyl)nicotinic acid

生成物 1

HCID 86712954
N-Cyclopropyl-6-(4-{1-[8-(hydroxymethyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-3-yl]cyclopropyl}phenyl)nicotinamide
収率 18%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of the compound (150 mg, 0.344 mmol) obtained in Example 66, cyclopropylamine (119 μL, 1.72 mmol), N,N-dimethylaminopyridine (4 mg, 34 μmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (198 mg, 1.03 mmol) in N,N-dimethylformamide (3.00 mL) was stirred at room temperature for 5 h. Saturated aqueous sodium hydrogencarbonate (100 mL) was added to the reaction mixture, the mixture was extracted with dichloromethane, and the organic layer was washed with water and dried with anhydrous sodium sulfate. Then the solvent was distilled off under reduced pressure. Diisopropyl ether was added to the residue, and the precipitate was collected by filtration and purified by silica gel column chromatography (ethyl acetate:methanol=1:4) to obtain the title compound (29 mg, 18%) as a white solid.

後処理

  1. extractionthe mixture was extracted with dichloromethane
  2. washthe organic layer was washed with water
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationThen the solvent was distilled off under reduced pressure
  5. additionDiisopropyl ether was added to the residue
  6. filtrationthe precipitate was collected by filtration
  7. custompurified by silica gel column chromatography (ethyl acetate:methanol=1:4)

出典と根拠

ORDレコード
ord-99cbb6eb92d04bd6b6552f82b2f76e31
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08927536B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート