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

HRID 2195074Notes

Reaction equation

HRID 2195074 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-72765fd1bb22485b8bdda07012898d82
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

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