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p-Toluenesulfonic acid monohydrate → 7-Chloro-1-{[(1R,2R)-2-methyl-4-oxocyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

HRID 1971008
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HRID 1971008 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:14]([NH:15][C@@H:16]4[CH2:25][CH2:24][C:19]5(OCC[O:20]5)[CH2:18][C@H:17]4[CH3:26])=[N:13][CH:12]=[C:11]([C:27]#[N:28])[C:7]=3[NH:8][C:9]=2[CH:10]=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>CC(C)=O.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:14]([NH:15][C@@H:16]4[CH2:25][CH2:24][C:19](=[O:20])[CH2:18][C@H:17]4[CH3:26])=[N:13][CH:12]=[C:11]([C:27]#[N:28])[C:7]=3[NH:8][C:9]=2[CH:10]=1
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참가 물질

5

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 686692527-Chloro-1-{[(7R,8R)-7-methyl-1,4-dioxaspiro[4.5]dec-8-yl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

생성물 1

HCID 686696457-Chloro-1-{[(1R,2R)-2-methyl-4-oxocyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

시약·촉매·용매 2

HCID 180Acetone용매HCID 8857Ethyl Acetate
용매

실험 절차

To a stirred solution of 7-chloro-1-{[(7R,8R)-7-methyl-1,4-dioxaspiro[4.5]dec-8-yl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile (147 mg, 0.37 mmol) in acetone (15 mL) was added pTsOH.H2O (176 mg, 0.93 mmol). The mixture was left to stir overnight, diluted with EtOAc, and washed with aqueous sodium bicarbonate solution. The organic layer was dried (sodium sulfate), and concentrated to afford the title compound. LRMS (APCI) calc'd for (C19H17ClN4O) [M+H]+, 353.1. found 353.0.

후처리

  1. waitThe mixture was left
  2. washwashed with aqueous sodium bicarbonate solution
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a94490514eef411e98461c090881f17b
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08431569B2

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