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Triethylamine → N-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-(phenylsulfonylmethyl)cyclohexyl)-3-(pyridin-3-yl)propanamide

HRID 641596
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HRID 641596 반응식
[CH:1]([N:4]([CH3:22])[C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH2:11])[C@H:7]([CH2:12][S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:6]1)([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.CCN(CC)CC.[N:53]1[CH:58]=[CH:57][CH:56]=[C:55]([CH2:59][CH2:60][C:61](O)=[O:62])[CH:54]=1>C(Cl)Cl>[CH:1]([N:4]([CH3:22])[C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:61](=[O:62])[CH2:60][CH2:59][C:55]2[CH:54]=[N:53][CH:58]=[CH:57][CH:56]=2)[C@H:7]([CH2:12][S:13]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)(=[O:14])=[O:15])[CH2:6]1)([CH3:3])[CH3:2]
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참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 2596243-(Pyridin-3-yl)propanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68468828(1R*,3R*,4S*)-N1-isopropyl-N1-methyl-3-(phenylsulfonylmethyl)cyclohexane-1,4-diamine

생성물 1

HCID 11431032
N-((1S,2R,4R)-4-(isopropyl(methyl)amino)-2-(phenylsulfonylmethyl)cyclohexyl)-3-(pyridin-3-yl)propanamide
수율 66%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of (1R,3R,4S)-N1-isopropyl-N1-methyl-3-(phenylsulfonylmethyl)-cyclohexane-1,4-diamine (see 30b) (50 mg, 0.154 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (32 mg, 0.166 mmol), 1-hydroxybenzotriazole hydrate (HOBT) (22 mg, 0.166 mmol), Et3N (17 mg, 0.166 mmol) and 3-(pyridin-3-yl)propanoic acid (26 mg, 0.166 mmol) in CH2Cl2 (5 mL) was stirred overnight at room temperature. The mixture was dilute with CH2Cl2 (20 mL) and washed with water, brine and evaporated. The residue was chromatographed on silica gel (4-6% NH4OH/MeOH/CH2Cl2) to give the product (45 mg, 66%). MS found: (M+1)+: 458.53.

후처리

  1. washwashed with water, brine
  2. customevaporated
  3. customThe residue was chromatographed on silica gel (4-6% NH4OH/MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-bdf2315617d841ad831f62ca574684f4
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07696205B2

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