2-(2-(6-((R)-1-((S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl)-2,2,2-trifluoroethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-7-yloxy)ethyl acetate → 2-(2-(6-((R)-1-((S)-3-aminopyrrolidin-1-yl)-2,2,2-trifluoroethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoro quinolin-7-yloxy)ethyl acetate

HRID 338935Notes

Reaction equation

HRID 338935 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([C:18]3[N:22]4[CH:23]=[C:24]([C@@H:27]([N:32]5[CH2:36][CH2:35][C@H:34]([NH:37]C(OC(C)(C)C)=O)[CH2:33]5)[C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:26][C:21]4=[N:20][N:19]=3)=[N:15]2)=[CH:10][C:9]=1[F:45])(=[O:3])[CH3:2]>C(O)(C(F)(F)F)=O>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([C:18]3[N:22]4[CH:23]=[C:24]([C@@H:27]([N:32]5[CH2:36][CH2:35][C@H:34]([NH2:37])[CH2:33]5)[C:28]([F:29])([F:31])[F:30])[CH:25]=[CH:26][C:21]4=[N:20][N:19]=3)=[N:15]2)=[CH:10][C:9]=1[F:45])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 709830682-(2-(6-((R)-1-((S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl)-2,2,2-trifluoroethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-7-yloxy)ethyl acetate

Product 1

HCID 710051792-(2-(6-((R)-1-((S)-3-aminopyrrolidin-1-yl)-2,2,2-trifluoroethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoro quinolin-7-yloxy)ethyl acetateYield 80.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-(2-(6-((R)-1-((S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl)-2,2,2-trifluoroethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-7-yloxy)ethyl acetate (40 mg, 0.063 mmol) was stirred in TFA (3 mL) for 1 hour and then concentrated. The residue was dissolved in minimum methanol and added dropwise to a 4N HCl in ether solution. The resulting solid was filtered and dried to yield 2-(2-(6-((R)-1-((S)-3-aminopyrrolidin-1-yl)-2,2,2-trifluoroethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoro quinolin-7-yloxy)ethyl acetate (27 mg, 80% yield) hydrochloride as an off-white solid. LCMS APCI (+) m/z 505 (M+H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in minimum methanol
  3. additionadded dropwise to a 4N HCl in ether solution
  4. filtrationThe resulting solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-76a626c6f9e240418a99a7df25da1819
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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