Hydrochloric Acid → Methyl 3-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-5-hydroxy-benzoate

HRID 2241942Notes

Reaction equation

HRID 2241942 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl[C:14]1[N:15]=[CH:16][C:17]([C:20]([N:22]([CH3:24])[CH3:23])=[O:21])=[N:18][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>C(OCC)C.O.CS(C)=O>[CH3:23][N:22]([CH3:24])[C:20]([C:17]1[N:18]=[CH:19][C:14]([O:1][C:2]2[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[N:15][CH:16]=1)=[O:21]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 75076Methyl 3,5-DihydroxybenzoateHCID 590004705-chloro-N,N-dimethylpyrazine-2-carboxamide

Product 1

HCID 59205093Methyl 3-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-5-hydroxy-benzoate

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

To methyl 3,5-dihydroxybenzoate (CAS no. 2150-44-9) (85 g, 0.49 mol) was added 5-chloro-N,N-dimethyl-pyrazine-2-carboxamide (88.9 g, 0.48 mol), DMSO (1000 mL,) and cesium carbonate (418 g, 1.2 mol) and the mixture was heated to 50° C. for 3 hours. Water (1577 mL,) was charged followed by diethyl ether (540 mL). To the aqueous layer was charged 5M hydrochloric acid solution (395 mL, 1.97 mol) and the resulting white solid was filtered washed with water (2×311 mL) and dried under vacuum at 40° C. over P2O5 overnight to give the desired compound (143 g).

Workup

  1. filtrationthe resulting white solid was filtered
  2. washwashed with water (2×311 mL)
  3. dry with materialdried under vacuum at 40° C. over P2O5 overnight

Sources & evidence

ORD record
ord-fd2b260d70e54c68ba1101538206f108
Source dataset
uspto-grants-2010_03
Patent number
US07671060B2

Reaction notes

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