1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 46852902, 화합물

HRID 421788노트

반응식

HRID 421788 반응식
[CH:1]([N:4]([C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21]([OH:23])=O)[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2].O.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[CH2:49]1[NH:54][CH2:53][CH2:52][N:51]2[CH2:55][CH2:56][CH2:57][C@H:50]12>ClCCl.CN(C)C=O.ClCCl>[CH2:49]1[N:54]([C:21]([C:20]2[CH:19]=[C:18]([N:4]([CH:1]([CH3:3])[CH3:2])[S:5]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=3)(=[O:7])=[O:6])[CH:26]=[CH:25][CH:24]=2)=[O:23])[CH2:53][CH2:52][N:51]2[CH2:55][CH2:56][CH2:57][C@H:50]12

참가 물질

7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 7004239(8aR)-Octahydropyrrolo(1,2-a)pyrazineHCID 66676232HCID 66676232, 화합물

생성물 1

HCID 46852902HCID 46852902, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 22350042dichloromethane N,N-dimethylformamide용매

실험 절차

To a mixture of 3-(N-isopropyl-3-(trifluoromethyl)phenylsulfonamido)benzoic acid (155 mg, 0.4 mmol) and 1-hydroxybenzotriazole hydrate (61 mg, 0.4 mmol) in dichloromethane/N,N-dimethylformamide (4:1, 6 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC, 62 mg, 0.4 mmol) in dichloromethane (1 mL). After 5 minutes, (R)-octahydropyrrolo[1,2-a]pyrazine (50 mg, 0.4 mmol) in dichloromethane (1 mL) was added. The mixture was stirred at room temperature overnight. Then the mixture was concentrated. The residue was diluted with ethyl acetate (100 mL), washed with water (2×20 mL), dried over sodium sulfate, and concentrated. The residue was purified by chromatography on silica gel (dichloromethane, then methanol/dichloromethane=1:12) to give the titled compound: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.00 (d, 6H, J=8 Hz), 1.35 (m, 1H), 1.65-2.10 (m, 6H), 2.80-3.05 (m, 4H), 3.45-3.55 (m, 1H), 4.40-4.50 (m, 1H), 4.60 (m, 1H), 6.98 (s, 1H), 7.15 (m, 1H), 7.50 (m, 2H), 7.88 (m, 2H), 8.10 (m, 2H); MS (ESI) m/z 496 (M+H)+.

후처리

  1. concentrationThen the mixture was concentrated
  2. additionThe residue was diluted with ethyl acetate (100 mL)
  3. washwashed with water (2×20 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (dichloromethane

출처 및 근거

ORD 기록
ord-41027878ee214c8cb8e78b61183d1b37
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101614B2

반응 노트

불러오는 중…