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

HRID 1971008Notes

Reaction equation

HRID 1971008 reaction equation
[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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-a94490514eef411e98461c090881f17b
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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