3-Aminopyridine → HCID 44222110, compound

HRID 655800Notes

Reaction equation

HRID 655800 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2/[CH:11]=[CH:12]/[C:13]1[CH:14]=[C:15]([NH:20][C:21](=[O:32])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH:16]=[CH:17][C:18]=1[CH3:19].[NH2:33][C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.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]>[CH3:19][C:18]1[CH:17]=[CH:16][C:15]([NH:20][C:21](=[O:32])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)=[CH:14][C:13]=1/[CH:12]=[CH:11]/[N:6]1[CH:5]=[N:4][C:3]2[C:7]1=[N:8][CH:9]=[N:10][C:2]=2[NH:33][C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1

Participants

7

Reactant 4

HCID 100093-AminopyridineHCID 62657Potassium Phosphate, TribasicHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 44222282HCID 44222282, compound

Product 1

HCID 44222110HCID 44222110, compound

Reagents, catalysts & solvents 2

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

Procedure

(E)-N-(3-(2-(6-Chloro-9H-purin-9-yl)vinyl)-4-methylphenyl)-3-(trifluoromethyl)benzamide (0.046 g, 0.10 mmol), 3-aminopyridine (0.022 g, 0.22 mmol), Pd2(dba)3 (5 mol %), 2-(dicyclohexylphosphino)biphenyl (7.5 mol %) and K3PO4 (0.032 g, 0.15 mmol) were mixed in DME. The mixture was heated at reflux under N2 for 15 h, cooled to rt, and partitioned between aq. Na2CO3 and EtOAc. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, concentrated on a rotavap, and then purified by RP HPLC (acetonitrile/water/0.1% TFA): MS [M+H]+ 515.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under N2 for 15 h
  3. custompartitioned between aq. Na2CO3 and EtOAc
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated on a rotavap
  7. custompurified by RP HPLC (acetonitrile/water/0.1% TFA)

Sources & evidence

ORD record
ord-ac84a4c3a15f43e1870ef18a7eefe3be
Source dataset
uspto-grants-2011_12
Patent number
US08071609B2

Reaction notes

Loading…