Methyl(6-methyl-2-pyridylmethyl)amine → HCID 69730740, compound

HRID 2182166Notes

Reaction equation

HRID 2182166 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[N:18][CH:17]=[C:16](Cl)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:21][NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.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]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[N:18][CH:17]=[C:16]([N:22]([CH3:21])[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=3)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 81438Methyl(6-methyl-2-pyridylmethyl)amineHCID 634876Binap, (A+-)-HCID 18186946Tert-butyl 4-(6-chloropyrazin-2-YL)piperazine-1-carboxylateHCID 23676156Sodium t-butoxide

Product 1

HCID 69730740HCID 69730740, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6′-chloro-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester I-1a (50 mg, 0.17 mmol), methyl-(6-methyl-pyridin-2-ylmethyl)-amine (29.6 mg, 0.22 mmol), sodium tert-butoxide (45 mg, 0.46 mmol), BINAP (8.4 mg, 0.014 mmol), tris(dibenzylideneacetone)dipalladium(0) (6.2 mg, 0.006 mmol) in toluene (2 mL) was stirred at reflux for 2 h. The reaction mixture was cooled, diluted with ethyl acetate, and filtered through celite. The filtrate was concentrated in vacuo and the residue was purified via preparative TLC (5% methanol in methylene chloride) to yield the title compound I-4g (14.2 mg).

Workup

  1. temperatureat reflux for 2 h
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified via preparative TLC (5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-47237264645644d484a6381ee0265e31
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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