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

HRID 2308535ノート

反応式

HRID 2308535 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
5 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-25ecdad69f334aca9e418d080f7181d0
出典データセット
uspto-grants-2004_12
特許番号
US06835732B2

反応ノート

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