Water → HCID 86732559, compound

HRID 711411Notes

Reaction equation

HRID 711411 reaction equation
CS(O[CH2:6][CH2:7][CH:8]1[N:13]2[CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)[CH:16]=[C:12]2[C:11](=[O:24])[NH:10][CH2:9]1)(=O)=O.[N-:25]=[N+:26]=[N-:27].[Na+].O.C([O-])(O)=O.[Na+]>C(#N)C.CN(C=O)C>[N:25]([CH2:6][CH2:7][CH:8]1[N:13]2[CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)[CH:16]=[C:12]2[C:11](=[O:24])[NH:10][CH2:9]1)=[N+:26]=[N-:27]

Participants

6

Reactant 4

HCID 962WaterHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 86732557HCID 86732557, compound

Product 1

HCID 86732559HCID 86732559, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

2-[1-oxo-7-(3-chlorophenyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]ethyl methanesulfonate 157 mg (0.42 mmol) were reacted with sodium azide (60 mg 0.924 mmol) in acetonitrile/DMF 10 ml/2 ml at 80° C. for 18 hours. The reaction was worked up with water, saturated NaHCO3 and extracted with ethyl acetate. The organic phase, dried on Na2SO4, was filtered and evaporated. The crude was dissolved with diethyl ether and after a while, a solid precipitated, which was filtered to give 92 mg (70%) of 4-(2-azidoethyl)-7-(3-chlorophenyl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase, dried on Na2SO4
  3. filtrationwas filtered
  4. customevaporated
  5. dissolutionThe crude was dissolved with diethyl ether
  6. customafter a while, a solid precipitated
  7. filtrationwhich was filtered

Sources & evidence

ORD record
ord-c3d00152f3f84c048172babc5c78d42f
Source dataset
uspto-grants-2015_11
Patent number
US09181258B2

Reaction notes

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