Piperidine → [8-Methyl-3-(1-{4-[5-(piperidin-1-ylcarbonyl)pyridin-2-yl]phenyl}cyclopropyl)-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-8-yl]methanol

HRID 1424134ノート

反応式

HRID 1424134 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](O)=[O:27])=[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.[NH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:31][C:3]1([CH2:2][OH:1])[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]([N:32]6[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]6)=[O:27])=[CH:24][N:23]=5)=[CH:18][CH:17]=4)[CH2:14][CH2:15]3)=[N:11][N:12]=[C:5]2[CH2:4]1

参加物

6

反応物 4

HCID 8082PiperidineHCID 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 86712979[8-Methyl-3-(1-{4-[5-(piperidin-1-ylcarbonyl)pyridin-2-yl]phenyl}cyclopropyl)-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepin-8-yl]methanol収率 11.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of the compound (200 mg, 0.458 mmol) obtained in Example 66, piperidine (210 μL, 2.29 mmol), N,N-dimethylaminopyridine (6 mg, 46 μmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (264 mg, 1.37 mmol) in N,N-dimethylformamide (4.00 mL) was stirred at room temperature for 6 h. Saturated aqueous sodium hydrogencarbonate (100 mL) was added to the reaction mixture, the mixture was extracted with dichloromethane/2-propanol (4/1), and the organic layer was washed with water and dried with anhydrous sodium sulfate. Then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1 to 4:1) to obtain the title compound (26 mg, 11%) as a white solid.

後処理

  1. extractionthe mixture was extracted with dichloromethane/2-propanol (4/1)
  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. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1 to 4:1)

出典と根拠

ORDレコード
ord-9b1c882d78f14ef6b5ef109f7f50c200
出典データセット
uspto-grants-2015_01
特許番号
US08927536B2

反応ノート

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