Hydrogen Peroxide → 8-fluoro-1-[(3-fluoro-4-hydroxycyclohexyl)amino]-5H-pyrido[4,3-b]indole-4-carboxamide

HRID 1971021Notes

Reaction equation

HRID 1971021 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]([C:24]#[N:25])=[CH:12][N:13]=[C:14]([NH:15][CH:16]4[CH2:21][CH2:20][CH:19]([OH:22])[CH:18]([F:23])[CH2:17]4)[C:5]=3[C:4]=2[CH:3]=1.OO.C(=O)([O-])[O-:29].[K+].[K+]>CS(C)=O>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]([C:24]([NH2:25])=[O:29])=[CH:12][N:13]=[C:14]([NH:15][CH:16]4[CH2:21][CH2:20][CH:19]([OH:22])[CH:18]([F:23])[CH2:17]4)[C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 595431238-fluoro-1-[(3-fluoro-4-hydroxycyclohexyl)amino]-5H-pyrido[4,3-b]indole-4-carbonitrile

Product 1

HCID 426360498-fluoro-1-[(3-fluoro-4-hydroxycyclohexyl)amino]-5H-pyrido[4,3-b]indole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 8-fluoro-1-[(3-fluoro-4-hydroxycyclohexyl)amino]-5H-pyrido[4,3-b]indole-4-carbonitrile (72 mg, 0.21 mmol) in DMSO were added hydrogen peroxide (30%, 0.18 mL, 2.10 mmol) and potassium carbonate (157 mg, 1.14 mmol). The reaction mixture was heated to 70° C. for 4 h, cooled to room temperature, filtered, and purified by prep-HPLC to afford the title compound. 1H NMR (500 MHz, CD3OD) δ 8.48 (s, 1H); 7.92 (dd, 1H); 7.57 (dd, 1H); 7.16 (dt, 1H); 4.35-4.52 (m, 2H); 3.71 (m, 1H); 1.46-2.55 (series of m, 6H). LRMS (APCI) calc'd for (C18H18F2N4O2) [M+H]+, 361.1. found 361.0.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-2210e81761ac4a218e8f4d68868490b5
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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