Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate → HCID 86605364, compound

HRID 1444139Notes

Reaction equation

HRID 1444139 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH:15]3[CH3:20])[N:11]=[C:10]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][C@H:22]3[CH3:27])[N:9]=2)=[CH:4][CH:3]=1.[CH3:28][O:29][C:30]([C:32]1[C:37]([NH2:38])=[N:36][C:35](Cl)=[C:34]([Cl:40])[N:33]=1)=[O:31]>C(O)(C)C>[CH3:28][O:29][C:30]([C:32]1[N:33]=[C:34]([Cl:40])[C:35]([N:17]2[CH2:18][CH2:19][N:14]([C:12]3[CH:13]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[N:9]=[C:10]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][C@H:22]4[CH3:27])[N:11]=3)[CH:15]([CH3:20])[CH2:16]2)=[N:36][C:37]=1[NH2:38])=[O:31]

Participants

4

Reactant 2

HCID 73828Methyl 3-amino-5,6-dichloropyrazine-2-carboxylateHCID 66838894HCID 66838894, compound

Product 1

HCID 86605364HCID 86605364, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Heat a mixture of 4-[4-(4-fluoro-phenyl)-6-(2-methyl-piperazin-1-yl)-pyrimidin-2-yl]-3-(R)-methyl-morpholine with 1.1 equivalents of 3-amino-5,6-dichloro-pyrazine-2-carboxylic acid methyl ester (Cragoe et. al. J. Med. Chem., 1967, 10, 66-75) in isopropanol at 85° C. for 12 h. Concentrate the mixture under reduced pressure, and then partition between 10% NaOH and EtOAc. Dry the organic layer (Na2SO4) and concentrate under reduced pressure to give the title compound.

Workup

  1. temperatureHeat
  2. concentrationConcentrate the mixture under reduced pressure
  3. custompartition between 10% NaOH and EtOAc
  4. dry with materialDry the organic layer (Na2SO4)
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-e8550063b8b04a3ba4b67fdd63d0d14c
Source dataset
uspto-grants-2010_02
Patent number
US07662830B2

Reaction notes

Loading…