4-Fluoropiperidine → HCID 67020644, compound

HRID 550509

Reaction equation

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

Participants

Reactant 2

HCID 27591594-Fluoropiperidine

HCID 11654890HCID 11654890, compound

Product 1

HCID 67020644HCID 67020644, compoundYield 43%

Procedure

The procedure described in Example 23 was repeated using 3-(2-chloroethoxy)-N-{3-chloro-4-[(6-methylpyridin-3-yl)oxy]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine (prepared as described in Example 16) and 4-fluoropiperidine to give the title compound in 43% yield; NMR Spectrum: 1.66-1.70 (m, 2H), 1.80-1.87 (m, 2H), 2.41-2.44 (m, 2H), 2.45 (s, 3H), 2.64-2.68 (m, 2H), 2.83 (t, 2H), 4.44 (t, 2H), 4.65 (dm, 1H), 7.20 (d, 1H), 7.25 (br s, 2H), 7.73 (d, 1H), 8.11 (s, 1H), 8.21 (s, 1H), 8.36 (s, 1H), 8.62 (br s, 1H); Mass Spectrum: 498 (MH+).

Sources & evidence

ORD record: ord-9a6d09fe549949c5bef23066fe962bd5
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947676B2

Linked notes

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