Trifluoroacetic acid → 6-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine

HRID 1674768Notes

Reaction equation

HRID 1674768 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]([F:35])([F:34])[C:10]1[N:14]2[N:15]=[C:16]([N:19]3[CH2:23][CH:22]4[CH2:24][N:25](C(OC(C)(C)C)=O)[CH2:26][CH:21]4[CH2:20]3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1>ClCCl>[CH2:20]1[CH:21]2[CH2:26][NH:25][CH2:24][CH:22]2[CH2:23][N:19]1[C:16]1[CH:17]=[CH:18][C:13]2[N:14]([C:10]([C:9]([F:34])([F:35])[F:8])=[N:11][N:12]=2)[N:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67339843HCID 67339843, compound

Product 1

HCID 673403076-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazineYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (15 mL, 194.70 mmol) was added to a mixture of tert-butyl 5-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (3 g, 7.53 mmol) and dichloromethane (60 mL). The resulting solution was stirred at ambient temperature for 1 hour and then evaporated to leave an involatile residue. The residue was purified by ion-exchange chromatography on an SCX column using aqueous ammonia (7M) in methanol as eluant to give 6-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (2.200 g, 98%) as a white solid that was used without further purification.

Workup

  1. customevaporated
  2. customto leave an involatile residue
  3. customThe residue was purified by ion-exchange chromatography on an SCX column

Sources & evidence

ORD record
ord-01423fffdb2d4c4cab17795e75a94077
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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