Trifluoroacetic acid → HCID 66585015, compound

HRID 589887Notes

Reaction equation

HRID 589887 reaction equation
[C:1]([C:4]1[C:5]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)=[C:6]([Br:20])[N:7]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][C:8]=12)(=[O:3])[NH2:2].FC(F)(F)C(O)=O>ClCCl>[Br:20][C:6]1[N:7]2[CH2:12][CH2:11][NH:10][CH2:9][C:8]2=[C:4]([C:1]([NH2:2])=[O:3])[C:5]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66585058HCID 66585058, compound

Product 1

HCID 66585015HCID 66585015, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.24 g (2.83 mmol) of tert-butyl 8-carbamoyl-6-bromo-7-(3-fluorophenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate in 10 ml of dichloromethane are added slowly 2.8 ml (28 mmol) of trifluoroacetic acid. After stirring for 1 hour at room temperature, the solvent is evaporated off under reduced pressure, the residue is taken up in water and the aqueous phase is basified by addition of aqueous ammonia. The solid formed is separated out by filtration and rinsed with water, to give 0.92 g of 6-bromo-7-(3-fluorophenyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxamide in the form of a beige-coloured powder after drying under reduced pressure in the presence of potassium hydroxide.

Workup

  1. customthe solvent is evaporated off under reduced pressure
  2. additionthe aqueous phase is basified by addition of aqueous ammonia
  3. customThe solid formed
  4. customis separated out by filtration
  5. washrinsed with water

Sources & evidence

ORD record
ord-8d12f4d6af09401a9df09c75a30cc147
Source dataset
uspto-grants-2016_01
Patent number
US09233965B2

Reaction notes

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