Potassium Carbonate → 1-(Cyclohexanecarbonyl)indoline-5-sulfonamide

HRID 528823

反応式

HRID 528823 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH:14]1([C:20](Cl)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+]>CC#N.CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH:14]1([C:20]([N:1]2[C:9]3[C:4](=[CH:5][C:6]([S:10]([NH2:13])(=[O:11])=[O:12])=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 75938Cyclohexanecarbonyl chlorideHCID 80272522,3-dihydro-1H-indole-5-sulfonamide2 回

生成物 1

HCID 606987421-(Cyclohexanecarbonyl)indoline-5-sulfonamide収率 20.1%

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of indoline-5-sulfonamide (Intermediate 54A, 100 mg, 0.50 mmol) in MeCN (5.0 mL) was added cyclohexanecarbonyl chloride (0.14 mL, 1.00 mmol) and K2CO3 (174 mg, 1.26 mmol). The resulting reaction mixture was stirred at room temperature overnight and then diluted with EtOAc and sat. aq. NaHCO3 solution. The organic layer was washed with 1 N aq. NaOH solution, followed by 10% aq. LiCl solution. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with CH2Cl2 to give the title compound (31 mg, 20%) as a white solid. 1H NMR (DMSO-d6) δ 8.16 (d, J=6.8 Hz, 1H), 7.64-7.60 (m, 2H), 7.19 (m, 2H), 4.22 (t, J=8.5 Hz, 2H), 3.21-3.16 (m, 2H), 2.62-2.55 (m, 1H), 1.91-1.65 (m, 5H), 1.45-1.16 (m, 5H); MS(ESI+) m/z 309.1 (M+H)+.

後処理

  1. customThe resulting reaction mixture
  2. washThe organic layer was washed with 1 N aq. NaOH solution
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with CH2Cl2

出典と根拠

ORDレコード
ord-1a274eb274754d368c893024268328f8
出典データセット
uspto-grants-2016_05
特許番号
US09346795B2

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