Trifluoroacetic acid → (Hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(2-(1-methyl-1H-1,2,4-triazol-5-yl)phenyl)methanone

HRID 1525103Notes

Reaction equation

HRID 1525103 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([N:15]2[CH2:19][CH:18]3[CH2:20][N:21](C(OC(C)(C)C)=O)[CH2:22][CH:17]3[CH2:16]2)=[O:14])=[N:5][CH:4]=[N:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:16]1[CH:17]2[CH2:22][NH:21][CH2:20][CH:18]2[CH2:19][N:15]1[C:13]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:6]1[N:2]([CH3:1])[N:3]=[CH:4][N:5]=1)=[O:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68161719tert-butyl 5-{[2-(1-methyl-1H-1,2,4-triazol-5-yl)phenyl]carbonyl}hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Product 1

HCID 67116371(Hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)(2-(1-methyl-1H-1,2,4-triazol-5-yl)phenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 60 (100 mg, 0.252 mmol), DCM (2.5 mL), TFA (0.5 mL) were stirred at room temperature for 2 h and then concentrated in vacuo. The residue was dissolved in DCM and treated with Dowex 550 A resin. After stirring for 2 h the resin was removed by filtration and the filtrate was concentrated in vacuo to a colorless oil which was taken on to the next step without further purification. MS (ESI) mass calculated for C16H19N5O, 297.16; m/z found, 298.0.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in DCM
  3. additiontreated with Dowex 550 A resin
  4. customwas removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo to a colorless oil which
  6. customwas taken on to the next step without further purification

Sources & evidence

ORD record
ord-97388e68722b483c8c5a433b53d8115f
Source dataset
uspto-grants-2015_07
Patent number
US09079911B2

Reaction notes

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