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Dimethylamine → 3-(1-{[2-(dimethylamino)ethyl]sulfonyl}-4-piperidinyl)-5-phenyl-1H-indole-7-carboxamide

HRID 2267510
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인쇄 미리보기

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HRID 2267510 반응식
Cl[CH2:2][CH2:3][S:4]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[C:21]3[C:16](=[C:17]([C:28]([NH2:30])=[O:29])[CH:18]=[C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:8]1)(=[O:6])=[O:5].[CH3:31][NH:32][CH3:33].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC#N>[CH3:31][N:32]([CH3:33])[CH2:2][CH2:3][S:4]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[C:21]3[C:16](=[C:17]([C:28]([NH2:30])=[O:29])[CH:18]=[C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:8]1)(=[O:6])=[O:5]
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참가 물질

6

반응물 4

HCID 674DimethylamineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 590033063-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide

생성물 1

HCID 114962033-(1-{[2-(dimethylamino)ethyl]sulfonyl}-4-piperidinyl)-5-phenyl-1H-indole-7-carboxamide수율 48.9%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

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온도
80 °C

실험 절차

To a solution of 3-{1-[(2-chloroethyl)sulfonyl]-4-piperidinyl}-5-phenyl-1H-indole-7-carboxamide (26 mg, 0.063 mmol) in CH3CN (5 mL), dimethylamine (0.16 mL, 0.315 mmol), K2CO3 (35 mg, 0.252 mmol) and NaI (cat. 0.5 mg) were added. The reaction mixture was stirred at 80° C. for 16 hours. The solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulfate, filtered and the solvent removed under reduced pressure. The resulting residue was purified by reverse phase HPLC (CH3CN/water, 0.1% TFA) to give title compound (14 mg, 48%).

후처리

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe resulting residue was purified by reverse phase HPLC (CH3CN/water, 0.1% TFA)

출처 및 근거

ORD 기록
ord-75ff698322674d04811461320869195c
출처 데이터셋
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07858796B2

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