Trifluoroacetic acid → HCID 67340155, compound

HRID 1675113Notes

Reaction equation

HRID 1675113 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]([F:35])([F:34])[C:10]1[N:14]2[N:15]=[C:16]([N:19]3[CH2:25][C@H:24]4[N:26](C(OC(C)(C)C)=O)[C@H:21]([CH2:22][CH2:23]4)[CH2:20]3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1>C(Cl)Cl.CO>[C@@H:24]12[NH:26][C@@H:21]([CH2:22][CH2:23]1)[CH2:20][N:19]([C:16]1[CH:17]=[CH:18][C:13]3[N:14]([C:10]([C:9]([F:35])([F:34])[F:8])=[N:11][N:12]=3)[N:15]=1)[CH2:25]2

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67339770HCID 67339770, compound

Product 1

HCID 67340155HCID 67340155, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

TFA (2.42 ml, 31.4 mmol) was added to a stirred solution of (1R,5S)-tert-butyl 3-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (443 mg, 1.11 mmol) in DCM (4.50 ml) at 25° C. The resulting solution was stirred at ambient temperature for 18 hours. The reaction mixture was diluted with methanol and the crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted using 7M ammonia in methanol and evaporated to dryness to afford 6-[(1R,5S)-3,8-diazabicyclo[3.2.1]oct-3-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (336 mg, 100%) as a white solid.

Workup

  1. customthe crude product was purified by ion exchange chromatography
  2. washThe desired product was eluted
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-44fdc0000d2a4794be8a6a1164c2e57e
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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