Hydrochloric Acid → 8-Fluoro-1-{[(1R,2R)-2-methyl-4-oxocyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

HRID 1971016Notes

Reaction equation

HRID 1971016 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]([C:27]#[N:28])=[CH:12][N:13]=[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])[C:5]=3[C:4]=2[CH:3]=1.Cl>CC(C)=O.CCOC(C)=O>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]([C:27]#[N:28])=[CH:12][N:13]=[C:14]([NH:15][C@@H:16]4[CH2:25][CH2:24][C:19](=[O:20])[CH2:18][C@H:17]4[CH3:26])[C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 686699758-Fluoro-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 686689758-Fluoro-1-{[(1R,2R)-2-methyl-4-oxocyclohexyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 8-fluoro-1-{[(7R,8R)-7-methyl-1,4-dioxaspiro[4.5]dec-8-yl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile (8.5 g, 22.3 mmol) in acetone (100 mL) was added HCl (1 M, 100 mL, 100 mmol). The mixture was heated to 50° C. for 1 h, diluted with EtOAc, and washed with 1 N NaOH. The organic layer was dried (sodium sulfate), and concentrated to afford the title compound. LRMS (APCI) calc'd for (C19H17FN4O) [M+H]+, 337.1. found 337.0.

Workup

  1. washwashed with 1 N NaOH
  2. dry with materialThe organic layer was dried (sodium sulfate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-164e8088b8a44457ad962adc98e5cf88
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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