Hydrochloric Acid → N-{5-(2-hydroxyethoxy)-2-[5-(thiomorpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylpyridine-2-sulfonamide

HRID 1960564ノート

反応式

HRID 1960564 の反応式
[CH3:1][N:2]([S:31]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)(=[O:33])=[O:32])[C:3]1[CH:4]=[C:5]([O:24][CH2:25][C:26](OCC)=[O:27])[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][N:18]3[CH2:23][CH2:22][S:21][CH2:20][CH2:19]3)[CH2:15][N:16]=1)=[CH:8]2.[BH4-].[Li+].Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[OH:27][CH2:26][CH2:25][O:24][C:5]1[CH:6]=[C:7]2[C:11](=[C:3]([N:2]([CH3:1])[S:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=3)(=[O:32])=[O:33])[CH:4]=1)[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][N:18]3[CH2:23][CH2:22][S:21][CH2:20][CH2:19]3)[CH2:15][N:16]=1)=[CH:8]2

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 59136117ethyl({7-[methyl(pyridin-2-ylsulfonyl)amino]-2-[5-(thiomorpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-5-yl}oxy)acetate

生成物 1

HCID 59135920N-{5-(2-hydroxyethoxy)-2-[5-(thiomorpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylpyridine-2-sulfonamide収率 55.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl ({7-[methyl(pyridin-2-ylsulfonyl)amino]-2-[5-(thiomorpholinomethyl)-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-5-yl}oxy)acetate (400 mg) in tetrahydrofuran (5 mL) was added lithium borohydride (18 mg) under ice-cooling, and the mixture was stirred at room temperature for 3 days. 1N Hydrochloric acid was added under ice-cooling, and the mixture was basified with saturated aqueous sodium hydrogencarbonate, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure: The residue was crystallized from ethyl acetate to give the title compound (205 mg, yield 55%) as a colorless solid. melting point 160-162° C.

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from ethyl acetate

出典と根拠

ORDレコード
ord-4290e0b06b9b4762b59ba781b4f0414d
出典データセット
uspto-grants-2013_04
特許番号
US08410087B2

反応ノート

読み込み中…