Hydrochloric Acid → (3-Amino-pyrazin-2-yl)-(4-chloro-phenyl)-methanone

HRID 2387204Notes

Reaction equation

HRID 2387204 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.C1COCC1.C1(C)C=CC=CC=1.CON(C)[C:25]([C:27]1[C:32]([NH2:33])=[N:31][CH:30]=[CH:29][N:28]=1)=[O:26].Cl>C1COCC1>[NH2:33][C:32]1[C:27]([C:25]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:26])=[N:28][CH:29]=[CH:30][N:31]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 22635083Tetrahydrofuran tolueneHCID 866345493-Amino-pyrazine-2-carboxylic acid methoxy-methylamideHCID 178478191HCID 178478191, compound

Product 1

HCID 68629738(3-Amino-pyrazin-2-yl)-(4-chloro-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.9 M 4-chlorophenyl magnesium bromide in THF/toluene (9.15 ml, 8.24 mmol) is added dropwise to a solution of 3-amino-pyrazine-2-carboxylic acid methoxy-methylamide (0.5 g, 2.74 mmol) in THF (15 ml) at 0° C. The reaction is allowed to warm to room temperature and stirred for 1.5 hours. The reaction mixture is cooled to 0° C. and 2 M HCl (20 ml) is added. The product is extracted into EtOAc (3×40 ml), dried (MgSO4) and concentrated in vacuo. Purification by flash chromatography (SiO2, 0-5% MeOH in DCM) yields (3-Amino-pyrazin-2-yl)-(4-chloro-phenyl)-methanone as a yellow solid.

Workup

  1. temperatureThe reaction mixture is cooled to 0° C.
  2. extractionThe product is extracted into EtOAc (3×40 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (SiO2, 0-5% MeOH in DCM)

Sources & evidence

ORD record
ord-ede9daa107f94e53b800887978d33ac7
Source dataset
uspto-grants-2012_09
Patent number
US08268834B2

Reaction notes

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