1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (+/-)-1-Benzyl-N-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpyrrolidine-3-carboxamide

HRID 1024498

반응식

HRID 1024498 반응식
Cl[C:2]1[C:7]2[O:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=[C:4]([CH2:13][NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH:3]=1.[CH2:19]([N:26]1[CH2:30][CH2:29][CH:28]([C:31]([OH:33])=O)[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.C(N=C=NCCCN(C)C)C.CC1C=CN=C(N)C=1C>ClCCl.O>[CH2:19]([N:26]1[CH2:30][CH2:29][CH:28]([C:31]([N:14]([CH2:13][C:4]2[CH:3]=[CH:2][C:7]3[O:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=3[CH:5]=2)[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:33])[CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

참가 물질

7

반응물 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 46173481-benzylpyrrolidine-3-carboxylic AcidHCID 110078842-Amino-3,4-dimethylpyridineHCID 43087680N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine

생성물 1

HCID 58080500(+/-)-1-Benzyl-N-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpyrrolidine-3-carboxamide

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

The above amine product, N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine (807 mg, 3 mmole) was combined with 1-Benzyl-pyrrolidine-3-carboxylic acid (615 mg, 3 mmole) in 50 ml dichloromethane. 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (764 mg, 4 mmole) and dimethyl aminopyridine (562 mg, 4 mmole) were added. The reaction solution was stirred at room temperature overnight. 50 ml of water was added and the mixture was extracted with 50 ml ethyl acetate three times. The organic layer was washed with saturated sodium bicarbonate, water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The product was purified by column chromatography using 50-75% ethyl acetate in hexane. MS (m+1)=457.3; H NMR (500 MHz, CDCl3) 0.95 (m, 6H), 2.00 (m, 1H), 2.05 (m, 1H), 2.15 (m, 1H), 2.25 (m, 1H), 2.55 (m, 1H), 2.65 (m, 1H), 2.90 (m, 1H), 3.00 (m, 1H), 3.10 (d, 1H), 3.15 (m, 1H), 3.25 (d, 1H), 3.40 (m, 1H), 3.75 (m, 2H), 4.30 (m, 4H), 4.45 (s, 1H), 4.55 (d, 1H), 6.6-7.0 (m, 2H), 7.2-7.5 (m, 5H).

후처리

  1. extractionthe mixture was extracted with 50 ml ethyl acetate three times
  2. washThe organic layer was washed with saturated sodium bicarbonate, water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified by column chromatography

출처 및 근거

ORD 기록
ord-89263181ac51444aa227ec54a2e8dd11
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722896B2

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