Diisopropylethylamine → HCID 86670956, 화합물

HRID 515319노트

반응식

HRID 515319 반응식
[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]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 18664284(3S)-oxolan-3-amine hydrochlorideHCID 86670955HCID 86670955, 화합물

생성물 1

HCID 86670956HCID 86670956, 화합물수율 45.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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]+

후처리

  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)

출처 및 근거

ORD 기록
ord-f691b1be7f4341a7987a6b0de5ba5f8c
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108939B2

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