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

Cesium carbonate → 5-(5-(4-Methoxyphenyl)-4-(1-methylpiperidin-4-ylamino)pyridin-2-ylamino)pyrazine-2-carbonitrile

HRID 556849
Notes
Print preview

Reaction equation

HRID 556849 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15](OC(C)(C)C)=O)[CH2:11][CH2:10]2)[C:5]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[CH:4][N:3]=1.Br[C:31]1[N:32]=[CH:33][C:34]([C:37]#[N:38])=[N:35][CH:36]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].COCCOC>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([C:5]2[C:6]([NH:8][CH:9]3[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]3)=[CH:7][C:2]([NH:1][C:31]3[N:32]=[CH:33][C:34]([C:37]#[N:38])=[N:35][CH:36]=3)=[N:3][CH:4]=2)=[CH:23][CH:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 378187222-Bromo-5-cyanopyrazineHCID 59613346Tert-butyl 4-(2-amino-5-(4-methoxyphenyl)pyridin-4-ylamino)piperidine-1-carboxylate

Product 1

HCID 596134065-(5-(4-Methoxyphenyl)-4-(1-methylpiperidin-4-ylamino)pyridin-2-ylamino)pyrazine-2-carbonitrile
Yield 20%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

Dry DME (402 μL) was added to a mixture of tert-butyl 4-(2-amino-5-(4-methoxyphenyl)pyridin-4-ylamino)piperidine-1-carboxylate (16 mg, 0.040 mmol), 5-bromopyrazine-2-carbonitrile (7.39 mg, 0.040 mmol), xantphos (1.859 mg, 3.21 μmol), tris(dibenzylideneacetone)dipalladium(0) (1.471 mg, 1.606 μmol), and cesium carbonate (26.2 mg, 0.080 mmol) in a nitrogen purged, sealed microwave vial. Nitrogen gas was bubbled through the mixture for 5 min. The reaction mixture was heated for 1 hr at 100° C. by microwave irradiation. Upon cooling the mixture was diluted with MeOH and purified by ion exchange on Isolute SCX II acidic resin (5 g), eluting with MeOH. The eluent was concentrated and further purified by preparative thin layer chromatography, eluting with 7% MeOH, 1% NH3, 92% DCM, to give 5-(5-(4-methoxyphenyl)-4-(1-methylpiperidin-4-ylamino)pyridin-2-ylamino)pyrazine-2-carbonitrile (4 mg, 7.97 μmol, 20% yield) as a light yellow powder.

Workup

  1. custompurged
  2. customsealed microwave vial
  3. customNitrogen gas was bubbled through the mixture for 5 min
  4. temperatureUpon cooling the mixture
  5. additionwas diluted with MeOH
  6. custompurified by ion exchange on Isolute SCX II acidic resin (5 g)
  7. washeluting with MeOH
  8. concentrationThe eluent was concentrated
  9. customfurther purified by preparative thin layer chromatography
  10. washeluting with 7% MeOH, 1% NH3, 92% DCM

Sources & evidence

ORD record
ord-b1a48c10002b479a89751c1a8ef5a6f6
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08058045B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes