Dichloromethane → 6-(difluoro(8-fluoro-6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)quinolin-3-ol

HRID 40349Notes

Reaction equation

C([O:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([C:19]([F:37])([F:36])[C:20]1[N:24]3[CH:25]=[C:26]([C:30]4[CH:31]=[N:32][N:33]([CH3:35])[CH:34]=4)[CH:27]=[C:28]([F:29])[C:23]3=[N:22][N:21]=1)=[CH:14][CH:13]=2)C1C=CC=CC=1.FC(F)(F)C(O)=O.C(Cl)Cl>CO>[F:37][C:19]([F:36])([C:20]1[N:24]2[CH:25]=[C:26]([C:30]3[CH:31]=[N:32][N:33]([CH3:35])[CH:34]=3)[CH:27]=[C:28]([F:29])[C:23]2=[N:22][N:21]=1)[C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][C:9]([OH:8])=[CH:18]2

Participants

Conditions

Temperature: 65 °C

Procedure

To a flask charged with 3-(benzyloxy)-6-(difluoro(8-fluoro-6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)quinoline (10 mg, 20 μmol) was added trifluoroacetic acid (1.5 mL, 20 mmol). The resulting solution was heated at 65° C. for 18 h. The solution was concentrated for purification by MPLC using 98:2 CH2Cl2: MeOH to 90:10 CH2Cl2: MeOH gradient to afford 6-(difluoro(8-fluoro-6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)quinolin-3-ol (3.6 mg, 44% yield) as a colorless solid. LRMS (ESI) m/z calcd for C20H14F3N6O (M+H) 411.1. found 411.3.

Workup

concentrationThe solution was concentrated for purification by MPLC

Sources & evidence

ORD record: ord-a20ca7a425b74a44959ffdcff6400c6d
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524900B2

Reaction notes

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