HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Dimethyl Sulfoxide → 7-Chloro-1-{[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-5H-pyrido[4,3-b]indole-4-carboxamide

HRID 1970995
Notes
Print preview

Reaction equation

HRID 1970995 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:14]([NH:15][C@H:16]([CH:21]4[CH2:23][CH2:22]4)[C:17]([F:20])([F:19])[F:18])=[N:13][CH:12]=[C:11]([C:24]#[N:25])[C:7]=3[NH:8][C:9]=2[CH:10]=1.C(=O)([O-])[O-:27].[K+].[K+].CS(C)=O.OO>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]([CH:21]4[CH2:22][CH2:23]4)[C:17]([F:18])([F:20])[F:19])=[N:13][CH:12]=[C:11]([C:24]([NH2:25])=[O:27])[C:7]=3[NH:8][C:9]=2[CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen Peroxide2×HCID 11430Potassium Carbonate2×HCID 565954467-Chloro-1-{[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile

Product 1

HCID 565954477-Chloro-1-{[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-5H-pyrido[4,3-b]indole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

7-Chloro-1-{[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-5H-pyrido[4,3-b]indole-4-carbonitrile (4.48 g, 12.3 mmol) and potassium carbonate (8.49 g, 61.4 mmol) were placed in a flask. DMSO (246 ml) and 30% hydrogen peroxide (12.55 ml, 123 mmol) were added and the solution heated at 80° C. for 2 h. Additional 30% hydrogen peroxide (12.55 mL, 123 mmol) and potassium carbonate (8.49 g, 61.4 mmol) were added. The resultant mixture was heated to 80° C. for 2 h, cooled to room temperature, and diluted with EtOAc. The mixture was washed with water and brine, dried (magnesium sulfate), concentrated, and purified by flash chromatography to give the title compound. 1H NMR (600 MHz, CD3SOCD3) δ 11.81 (s, 1H); 8.54 (s, 1H); 8.50 (d, 1H); 7.96 (br s, 1H); 7.80 (d, 1H); 7.33 (br s, 1H); 7.30 (dd, 1H); 7.07 (d, 1H); 4.86 (m, 1H); 1.59 (m, 1H); 0.76 (m, 1H); 0.64 (m, 1H); 0.54 (m, 1H); 0.33 (m, 1H). LRMS (APCI) calc'd for (C17H14ClF3N4O) [M+H]+, 383.1. found 383.0.

Workup

  1. temperaturecooled to room temperature
  2. washThe mixture was washed with water and brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-e479cc9172544887b104ae063f7f640c
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08431569B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes