Triethylamine → N-((6-cyclopropyl-2-m-tolylpyridin-3-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanamide

HRID 1428725노트

반응식

HRID 1428725 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:18])[C:15]([OH:17])=O)[CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][S:10]([CH3:13])(=[O:12])=[O:11].[CH:19]1([C:22]2[N:27]=[C:26]([C:28]3[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=3)[C:25]([CH2:35][NH2:36])=[CH:24][CH:23]=2)[CH2:21][CH2:20]1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>O1CCOCC1.C(OC(=O)C)C>[CH:19]1([C:22]2[N:27]=[C:26]([C:28]3[CH:29]=[C:30]([CH3:34])[CH:31]=[CH:32][CH:33]=3)[C:25]([CH2:35][NH:36][C:15](=[O:17])[CH:14]([C:4]3[CH:5]=[CH:6][C:7]([CH2:8][NH:9][S:10]([CH3:13])(=[O:11])=[O:12])=[C:2]([F:1])[CH:3]=3)[CH3:18])=[CH:24][CH:23]=2)[CH2:21][CH2:20]1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 866793652-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acidHCID 86680211(6-Cyclopropyl-2-m-tolylpyridin-3-yl)methanamine

생성물 1

HCID 71539635N-((6-cyclopropyl-2-m-tolylpyridin-3-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanamide수율 52%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

To a stirred solution of 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid (41 mg, 0.148 mmol) and (6-cyclopropyl-2-m-tolylpyridin-3-yl)methanamine (35 mg, 0.148 mmol) in dioxane were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (43 mg, 0.222 mmol), 1-hydroxybenzotriazole (30 mg, 0.222 mmol) and triethylamine (0.05 mL, 0.37 mmol). The reaction mixture was stirred for 15 h at room temperature. The residue dissolved in ethylacetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. N-((6-cyclopropyl-2-m-tolylpyridin-3-yl)methyl)-2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanamide (example 20) (38 mg) was obtained as 52% yield.

후처리

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate removed in vacuo
  5. customThe crude was purified by column chromatography

출처 및 근거

ORD 기록
ord-5bdc4ced22f742bfbc741e0ffdb06e27
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937092B2

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