Potassium Carbonate → (1R,6S)-8-(3-Methylpyrazin-2-yl)-3,8-diazabicyclo[4.2.0]octane

HRID 1193083Notes

Reaction equation

HRID 1193083 reaction equation
FC(F)(F)C1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[C@@H:16]3[C@@H:11]([CH2:12][CH2:13][NH:14][CH2:15]3)[CH2:10]2)N=1.ClC1N=C(C(F)(F)F)[CH:23]=[CH:22][N:21]=1.C([O-])([O-])=O.[K+].[K+].CCN(C(C)C)C(C)C>C(#N)C.CN(C=O)C>[CH3:23][C:22]1[C:5]([N:9]2[C@@H:16]3[C@@H:11]([CH2:12][CH2:13][NH:14][CH2:15]3)[CH2:10]2)=[N:6][CH:7]=[CH:8][N:21]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 67116508HCID 67116508, compound

Product 1

HCID 67116913(1R,6S)-8-(3-Methylpyrazin-2-yl)-3,8-diazabicyclo[4.2.0]octane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared in a manner analogous to Intermediate 27, substituting 2-chloro-3-methylpyrazine for 2-chloro-4-(trifluoromethyl)pyrimidine. In addition, DMF and K2CO3 at 95° C. was used in place of DIPEA and ACN.

Workup

  1. customat 95° C.

Sources & evidence

ORD record
ord-288c73417fe44ba1a28da2a9cb500103
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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