1-(2-Amino-4-methoxyphenyl)ethan-1-one → N-(2-acetyl-5-methoxyphenyl)-4-Isopropyl-2-Thiazolecarboxamide

HRID 388660노트

반응식

HRID 388660 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].[CH:13]([C:16]1[N:17]=[C:18]([C:21](Cl)=[O:22])[S:19][CH:20]=1)([CH3:15])[CH3:14]>O1CCOCC1>[C:10]([C:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[NH:1][C:21]([C:18]1[S:19][CH:20]=[C:16]([CH:13]([CH3:15])[CH3:14])[N:17]=1)=[O:22])(=[O:12])[CH3:11]

참가 물질

4

반응물 2

HCID 106786151-(2-Amino-4-methoxyphenyl)ethan-1-oneHCID 575787964-(Propan-2-yl)-1,3-thiazole-2-carbonyl chloride

생성물 1

HCID 20773655N-(2-acetyl-5-methoxyphenyl)-4-Isopropyl-2-Thiazolecarboxamide수율 75%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

Under nitrogen, a solution of compound 201a (3 g, 1 eq.) in 1,4-dioxane (30 mL) was added at 0° C. to a solution of compound 214 (4.1 g, 1.2 eq.) in 1,4-dioxane. The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel to yield compound as a beige solid 217a in 75% yield. 1H NMR (CDCl3, 400 MHz): δ (ppm) (ppm) 1.43 (d, J=6.98 Hz, 6H), 2.65 (s, 3H), 3.26 (hep, J=6.98 Hz, 1H), 3.92 (s, 3H), 6.69 (dd, J=2.59 and 8.80 Hz, 1H), 7.2 (d, J=0.84, 1H), 7.87 (d, J=8.9 Hz, 1H), 8.58 (d, J=2.59 Hz, 1H), 13.5 (br s, 1H); MS (ESI, EI+): m/z=319 (MH+).

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-c419ef183910467b98bd014e0c54a1e7
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377962B2

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