Pyrrolidine → HCID 178508428, compound

HRID 2173706Notes

Reaction equation

HRID 2173706 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([NH:8][C:9]([C:11]2[C:16]([NH2:17])=[N:15][C:14]([C:18]([F:21])([F:20])[F:19])=[C:13](Br)[N:12]=2)=[O:10])[NH:6][N:7]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>C1COCC1>[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([NH:8][C:9]([C:11]2[C:16]([NH2:17])=[N:15][C:14]([C:18]([F:21])([F:20])[F:19])=[C:13]([N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[N:12]=2)=[O:10])[NH:6][N:7]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 178508420HCID 178508420, compound

Product 1

HCID 178508428HCID 178508428, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-amino-6-bromo-5-trifluoromethyl-pyrazine-2-carboxylic acid (5-trifluoromethyl-2H-pyrazol-3-yl)-amide (Example 1) (40 mg, 0.095 mmol) in dry THF (2 ml) was added pyrrolidine (7.89 μL, 0.095 mmol). The resulting mixture was heated using microwave radiation at 120° C. for 35 minutes. The reaction mixture was partitioned between EtOAc (50 ml) and water (30 ml) and the organic portion was separated, (MgSO4) and concentrated in vacuo to give the crude product as an orange oil. The crude product was purified using preparative TLC eluting with DCM: 1% MeOH to afford the title compound as an orange solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. customat 120° C.
  3. customfor 35 minutes
  4. customThe reaction mixture was partitioned between EtOAc (50 ml) and water (30 ml)
  5. customthe organic portion was separated
  6. concentration(MgSO4) and concentrated in vacuo
  7. customto give the crude product as an orange oil
  8. customThe crude product was purified
  9. washeluting with DCM

Sources & evidence

ORD record
ord-998f21a16cf64a118efcb073d01b93c4
Source dataset
uspto-grants-2015_06
Patent number
US09056867B2

Reaction notes

Loading…