Methanol → 2-chloro-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-6-methyl-isonicotinamide

HRID 2308535노트

반응식

HRID 2308535 반응식
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[C:6]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1.C(N(C(C)C)C(C)C)C.[Cl:28][C:29]1[CH:30]=[C:31]([CH:35]=[C:36]([CH3:38])[N:37]=1)[C:32](Cl)=[O:33].CO>C1COCC1.ClCCl>[Cl:28][C:29]1[CH:30]=[C:31]([CH:35]=[C:36]([CH3:38])[N:37]=1)[C:32]([NH:12][C:10]1[S:11][C:7]2[C:6]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=2[N:9]=1)=[O:33]

참가 물질

7

반응물 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 27821302-Chloro-6-methylpyridine-4-carbonyl chlorideHCID 114028614-Methoxy-7-morpholinobenzo[d]thiazol-2-amine

생성물 1

HCID 222831702-chloro-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-6-methyl-isonicotinamide수율 76.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
5 °C

실험 절차

To a stirred suspension of 4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine (13.3 g, 50.1 mmol) in THF (700 ml) was added N-ethyldiisopropylamine (21.3 ml, 125 mmol). The mixture was then cooled to 5° C. and a solution of 2-chloro-6-methyl-isonicotinoyl chloride (10.5 g, 55.1 mmol) in dichloromethane (350 ml) was added dropwise over 2 hours. The reaction mixture was then stirred overnight at 20° C. To this mixture was added methanol (40 ml) and stirring continued for ten minutes. The mixture was then concentrated in vacuo and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phases were then dried over Na2SO4 and the solvent evaporated. The crude product was then chromatographed over SiO2 (Merck 230-400 mesh) eluting with CH2Cl2/MeOH (98:2), the product fractions were pooled and the solvent evaporated, to afford the title compound as a brown solid (16.0 g, 76% yield), MS: m/e=421 (M{37Cl}+H+), 419 (M{35Cl}+H+).

후처리

  1. stirringstirring
  2. waitcontinued for ten minutes
  3. concentrationThe mixture was then concentrated in vacuo
  4. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
  5. dry with materialThe organic phases were then dried over Na2SO4
  6. customthe solvent evaporated
  7. customThe crude product was then chromatographed over SiO2 (Merck 230-400 mesh)
  8. washeluting with CH2Cl2/MeOH (98:2)
  9. customthe solvent evaporated

출처 및 근거

ORD 기록
ord-25ecdad69f334aca9e418d080f7181d0
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06835732B2

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