Chlorosuccinimide → 5-[(6,7-Dichloro-1-oxo-1,2-dihydropyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzonitrile

HRID 1172794Notes

Reaction equation

HRID 1172794 reaction equation
FC(F)(F)C([O-])=O.[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[O:17])[NH:15][CH:14]=[C:13]([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([F:34])=[C:23]([CH:33]=3)[C:24]([N:26]3CCC[NH2+]CC3)=O)[N:12]2[CH:35]=1.[Cl:36]C1C=C2C(=O)NC=C(CC3C=CC(F)=C(C=3)C#N)N2C=1.ClN1C(=O)CCC1=O>C1COCC1>[Cl:36][C:35]1[N:12]2[C:13]([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([F:34])=[C:23]([CH:33]=3)[C:24]#[N:26])=[CH:14][NH:15][C:16](=[O:17])[C:11]2=[CH:10][C:9]=1[Cl:8]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 686864115-[(7-Chloro-1-oxo-1,2-dihydropyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzonitrileHCID 686892094-{5-[(7-Chloro-1-oxo-1,2-dihydropyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl}-1,4-diazepan-1-ium trifluoroacetate

Product 1

HCID 252240505-[(6,7-Dichloro-1-oxo-1,2-dihydropyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 6, F5 (1 eq) and N-chlorosuccinimide (2 eq) in THF was stirred at RT. The solvent was removed under reduced pressure and the resulting crude was used as such in the next step without purification. MS (ES) C15H8Cl2FN3O requires: 335, found: 336 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customwithout purification

Sources & evidence

ORD record
ord-d2f68aff7fb94656ae179ce69d097b17
Source dataset
uspto-grants-2010_11
Patent number
US07834015B2

Reaction notes

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