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Hydrochloric Acid → 5-cyclopropyl-2-fluoro-N-(methylsulfonyl)-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzamide

HRID 1849597
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HRID 1849597 반응식
[CH:1]1([C:4]2[C:5]([O:14][CH2:15][C:16]3([C:22]([F:25])([F:24])[F:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:6][C:7]([F:13])=[C:8]([CH:12]=2)[C:9](O)=[O:10])[CH2:3][CH2:2]1.Cl.C(N=C=NCCCN(C)C)C.[CH3:38][S:39]([NH2:42])(=[O:41])=[O:40].Cl>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH:1]1([C:4]2[C:5]([O:14][CH2:15][C:16]3([C:22]([F:25])([F:24])[F:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:6][C:7]([F:13])=[C:8]([CH:12]=2)[C:9]([NH:42][S:39]([CH3:38])(=[O:41])=[O:40])=[O:10])[CH2:3][CH2:2]1
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참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 867034505-Cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acid

생성물 1

HCID 867034515-cyclopropyl-2-fluoro-N-(methylsulfonyl)-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzamide수율 62%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 5-cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acid (0.36 g, 1.00 mmol) in dichloromethane (20 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.29 g, 1.50 mmol) and 4-dimethylaminopyridine (0.28 g, 2.30 mmol). The reaction was stirred at ambient temperature for 10 minutes, methanesulfonamide (0.15 g, 1.56 mmol) was added and the stirring was continued at ambient temperature for 17 hours. 5% aqueous hydrochloric acid solution (10 mL) were added and diluted with ethyl acetate (100 mL), washed with water and brine; dried over anhydrous sodium sulfate and concentrated in vacuo. Purification of the residue by column chromatography (30% ethyl acetate in hexanes) afforded the title compound (0.27 g, 62%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 8.70 (br s, 1H), 7.59 (d, J=9.0 Hz, 1H), 6.59 (d, J=14.1 Hz, 1H), 4.12 (s, 2H), 3.39 (s, 3H), 2.03-1.88 (m, 3H), 1.76-1.63 (m, 5H), 1.48-1.23 (m, 3H), 0.94-0.87 (m, 2H), 0.64-0.58 (m, 2H); MS (ES−) m/z 436.2 (M−1).

후처리

  1. waitthe stirring was continued at ambient temperature for 17 hours
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by column chromatography (30% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-609d6e3f25a64664ba1815fce2fb0a69
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08952169B2

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