Diisopropylethylamine → N-((2-(3-chloro-4-fluorophenyl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanamide

HRID 1428721노트

반응식

HRID 1428721 반응식
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:10]2[C:15]([CH2:16][NH2:17])=[CH:14][CH:13]=[C:12]([C:18]([F:21])([F:20])[F:19])[N:11]=2)[CH:6]=[CH:7][C:8]=1[F:9].[F:22][C:23]1[CH:24]=[C:25]([CH:35]([CH3:39])[C:36](O)=[O:37])[CH:26]=[CH:27][C:28]=1[CH2:29][NH:30][S:31]([CH3:34])(=[O:33])=[O:32].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>O1CCCC1>[Cl:2][C:3]1[CH:4]=[C:5]([C:10]2[C:15]([CH2:16][NH:17][C:36](=[O:37])[CH:35]([C:25]3[CH:26]=[CH:27][C:28]([CH2:29][NH:30][S:31]([CH3:34])(=[O:32])=[O:33])=[C:23]([F:22])[CH:24]=3)[CH3:39])=[CH:14][CH:13]=[C:12]([C:18]([F:20])([F:21])[F:19])[N:11]=2)[CH:6]=[CH:7][C:8]=1[F:9]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86676125(2-(3-Chloro-4-fluorophenyl)-6-(trifluoromethyl)pyridin-3-yl)methanamine hydrochlorideHCID 866793652-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid

생성물 1

HCID 71539579N-((2-(3-chloro-4-fluorophenyl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of (2-(3-chloro-4-fluorophenyl)-6-(trifluoromethyl)pyridin-3-yl)methanamine hydrochloride (1.104 g, 3.632 mmol) and 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid (1 g, 3.632 mmol) in tetrahydrofuran (28 mL) was added 1-hydroxybenzotriazolhydrate (0.49 mL, 3.632 mmol), O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (1.166 g, 3.632 mmol) and N-ethyldiisopropylamine (1.852 mL, 10.896 mmol) and the reaction mixture was allowed to stir for 48 h. The reaction mixture was concentrated under reduced pressure and the solid obtained was purified by column chromatography (eluent:ethyl acetate/cyclohexane 2:1) to afford a white solid (example 16) (605 mg, 30%).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe solid obtained
  3. customwas purified by column chromatography (eluent:ethyl acetate/cyclohexane 2:1)
  4. customto afford a white solid (example 16) (605 mg, 30%)

출처 및 근거

ORD 기록
ord-809254c0d9794e1295949c7cd60ca446
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937092B2

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