Sodium hydride → tert-butyl 1-methyl-8-[(5-methylisoxazol-4-yl)sulfonyl]-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate

HRID 2423213

반응식

HRID 2423213 반응식
[CH3:1][CH:2]1[C:8]2=[C:9]3[C:13](=[CH:14][CH:15]=[C:7]2[O:6][CH2:5][CH2:4][N:3]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[NH:12][CH:11]=[CH:10]3.[H-].[Na+].[CH3:25][C:26]1[O:30][N:29]=[CH:28][C:27]=1[S:31](Cl)(=[O:33])=[O:32]>CN(C=O)C>[CH3:1][CH:2]1[C:8]2=[C:9]3[C:13](=[CH:14][CH:15]=[C:7]2[O:6][CH2:5][CH2:4][N:3]1[C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[N:12]([S:31]([C:27]1[CH:28]=[N:29][O:30][C:26]=1[CH3:25])(=[O:33])=[O:32])[CH:11]=[CH:10]3

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 27761415-Methyl-1,2-oxazole-4-sulfonyl chlorideHCID 67242740tert-Butyl 1-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate2회

생성물 1

HCID 67242535tert-butyl 1-methyl-8-[(5-methylisoxazol-4-yl)sulfonyl]-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate수율 26.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

tert-Butyl 1-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate (Intermediate 42, 25 mg, 0.083 mmol) was dissolved in DMF (1 mL) and sodium hydride (60% in mineral oil, 4.0 mg, 0.17 mmol) was added. The reaction mixture was stirred at room temperature for 15 minutes before 5-methyl-4-isoxazolesulfonyl chloride (21 mg, 0.11 mmol) was added. The reaction mixture was allowed to stir at room temperature overnight. The reaction was quenched by addition of water and the crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN) to give tert-butyl 1-methyl-8-[(5-methylisoxazol-4-yl)sulfonyl]-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate (0.010 g) which was dissolved in DCM (1 mL) and TFA (1 mL) was added. The reaction mixture was stirred at room temperature for 1 hour and the solvent was removed under reduced pressure. The crude material was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN) to give the title compound (1 mg). MS m/z 348 [M+H]+.

후처리

  1. additionwas added
  2. customThe reaction was quenched by addition of water
  3. customthe crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN)

출처 및 근거

ORD 기록
ord-ea9a98092d084cb49091653962e54b87
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960374B2

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