Hydrochloric Acid → HCID 68182434, compound

HRID 1623949Notes

Reaction equation

HRID 1623949 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[CH2:8][C@H:9]3[CH2:21][C@H:10]3[C:11]=2[N:12]([C:14]2[CH:19]=[N:18][C:17](Br)=[CH:16][N:15]=2)[N:13]=1)=[O:5])C.[CH3:22][O-:23].[Na+].O.Cl>CO>[CH3:22][O:23][C:17]1[N:18]=[CH:19][C:14]([N:12]2[C:11]3[C@@H:10]4[CH2:21][C@@H:9]4[CH2:8][C:7]=3[C:6]([C:4]([OH:3])=[O:5])=[N:13]2)=[N:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10942334Sodium MethoxideHCID 86669688HCID 86669688, compound

Product 1

HCID 68182434HCID 68182434, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

To a reaction vial containing (1aR,5aR)-2-(5-bromopyrazin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid ethyl ester (120 mg, 0.344 mmol) in methanol was added sodium methoxide (74 mg, 1.375 mmol). The reaction mixture was heated at 140° C. for 1 h under microwave irradiation, poured into water, acidified with HCl solution and extracted with solution of DCM:IPA (4:1). The combined organics were dried and concentrated to give the title compound (70 mg). LCMS m/z=273.3 [M+H]+.

Workup

  1. extractionextracted with solution of DCM:IPA (4:1)
  2. customThe combined organics were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-deb86113675943a9a27008d2fa3332f9
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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