Diisopropylethylamine → HCID 86670956、化合物

HRID 515319ノート

反応式

HRID 515319 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([OH:31])([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[C:32](Cl)(=O)[O:33]C1C=CC([N+]([O-])=O)=CC=1.Cl.[O:46]1[CH2:50][CH2:49][C@H:48]([NH2:51])[CH2:47]1.C(N(C(C)C)C(C)C)C>ClCCl>[F:26][C:23]([F:24])([F:25])[C:22]([C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:12]2[CH2:11][CH2:10][CH:9]([S:8][C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:32]([NH:51][C@H:48]4[CH2:49][CH2:50][O:46][CH2:47]4)=[O:33])=[CH:3][CH:4]=3)[CH2:14][CH2:13]2)=[CH:17][CH:18]=1)([OH:31])[C:27]([F:30])([F:29])[F:28]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 18664284(3S)-oxolan-3-amine hydrochlorideHCID 86670955HCID 86670955、化合物

生成物 1

HCID 86670956HCID 86670956、化合物収率 45.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(4-((4-(4-Aminophenylthio)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (1.076 mmol, 500 mg), and 4-nitrophenyl carbonochloridate (1.076 mmol, 217 mg) were combined in dichloromethane (10 mL) and the reaction mixture stirred at room temperature for 1 hour. (S)-Tetrahydrofuran-3-amine hydrochloride (2.153 mmol, 266 mg), and N-ethyl-N-isopropylpropan-2-amine (2.153 mmol, 0.356 mL, 278 mg) were added and the reaction mixture stirred for 30 minutes. The reaction mixture was washed with water, and the organic layer separated, dried, and concentrated under vacuum. The residue was purified by silica column chromatography (eluting with 0-10% methanol/dichloromethane gradient) to afford the title compound (284 mg). MS m/z 578.2 [M+H]+

後処理

  1. stirringthe reaction mixture stirred for 30 minutes
  2. washThe reaction mixture was washed with water
  3. customthe organic layer separated
  4. customdried
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica column chromatography (eluting with 0-10% methanol/dichloromethane gradient)

出典と根拠

ORDレコード
ord-f691b1be7f4341a7987a6b0de5ba5f8c
出典データセット
uspto-grants-2015_08
特許番号
US09108939B2

反応ノート

読み込み中…