Pyridine → 5-Methyl-thiophene-2-carboxylic acid (7-bromo-4-methoxybenzothiazol-2-yl)-amide

HRID 1062990노트

반응식

HRID 1062990 반응식
[NH2:1][C:2]1[S:3][C:4]2[C:10]([Br:11])=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[C:5]=2[N:6]=1.N1C=CC=CC=1.[CH3:20][C:21]1[S:25][C:24]([C:26](Cl)=[O:27])=[CH:23][CH:22]=1>ClCCl>[Br:11][C:10]1[C:4]2[S:3][C:2]([NH:1][C:26]([C:24]3[S:25][C:21]([CH3:20])=[CH:22][CH:23]=3)=[O:27])=[N:6][C:5]=2[C:7]([O:12][CH3:13])=[CH:8][CH:9]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 27600835-Methylthiophene-2-carbonyl chlorideHCID 222832007-Bromo-4-methoxy-1,3-benzothiazol-2-amine

생성물 1

HCID 865849105-Methyl-thiophene-2-carboxylic acid (7-bromo-4-methoxybenzothiazol-2-yl)-amide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-Amino-7-bromo-4-methoxybenzothiazol (2.33 g, 9 mmol) is dissolved in dichloromethane (100 ml) and at 0° C. treated with pyridine (2.2 ml, 27 mmol) and 5-methyl-thiophene-2-carbonyl chloride (2.2 g, 13.5 mmol). The reaction mixture is allowed to warm to room temperature and after stirring for additional 18 h quenched with water (100 ml). After separation of the phases, the aqueous phases are extracted twice with ethyl acetate. The combined organic layers are then washed with brine, dried and avaporated to dryness. Flash chromatography on silica (eluent ethyl acetate/cyclohexane 1:1 to 4:1) and final recrystallization from ethyl acetate affords the product as off-white solid. (34 mg, 69%). MS: m/e=384 (M+).

후처리

  1. customquenched with water (100 ml)
  2. customAfter separation of the phases
  3. extractionthe aqueous phases are extracted twice with ethyl acetate
  4. washThe combined organic layers are then washed with brine
  5. customdried
  6. customFlash chromatography on silica (eluent ethyl acetate/cyclohexane 1:1 to 4:1) and final recrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-b364f833212d4f4dbee98309439f950b
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06963000B2

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