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

HRID 2425488Notes

Reaction equation

HRID 2425488 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-040c84b68bcc47f6a2ee7b436bd3e6df
Source dataset
uspto-grants-2011_06
Patent number
US07964725B2

Reaction notes

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