Trifluoroacetic acid → HCID 24901189, compound

HRID 1890970Notes

Reaction equation

HRID 1890970 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([N:12]2[CH:16]=[C:15]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][C:23]([S:27][C:28]3[N:32]5[N:33]=[C:34]([CH3:37])[CH:35]=[CH:36][C:31]5=[N:30][N:29]=3)=[CH:22][CH:21]=4)[CH:14]=[N:13]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH:8]1[CH2:9][CH:10]([N:12]2[CH:16]=[C:15]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][C:23]([S:27][C:28]3[N:32]5[N:33]=[C:34]([CH3:37])[CH:35]=[CH:36][C:31]5=[N:30][N:29]=3)=[CH:22][CH:21]=4)[CH:14]=[N:13]2)[CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24901258HCID 24901258, compound

Product 1

HCID 24901189HCID 24901189, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-{4-[6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylsulfanyl)-quinolin-3-yl]-pyrazol-1-yl}-azetidine-1-carboxylic acid tert-butyl ester (65 mg, 0.126 mmol) was added 6 mL of (1:1) TFA:dichloromethane. The mixture was allowed to sit for 2 hours. The volatiles were removed by rotary evaporation and then methanol (6 mL) and MP-carbonate (500 mg, 3.18 mmol/g) were added. The resin was filtered and the volatiles were removed in vacuo to provide 3-(1-azetidin-3-yl-1H-pyrazol-4-yl)-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylsulfanyl)-quinoline as a yellow solid (quantitative yield).

Workup

  1. customThe volatiles were removed by rotary evaporation
  2. additionmethanol (6 mL) and MP-carbonate (500 mg, 3.18 mmol/g) were added
  3. filtrationThe resin was filtered
  4. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-5b6ecc561e4e492dba4afa528e2f3980
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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