Sodium Bicarbonate → 2-(4-{[4-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl]methyl}phenyl)-3-phenyl-1,6-naphthyridin-5(6H)-one

HRID 604995Notes

Reaction equation

C[O:2][C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:7]([C:13]1[CH:35]=[CH:34][C:16]([CH2:17][N:18]3[CH2:23][CH2:22][CH:21]([N:24]4[C:28]5=[N:29][CH:30]=[N:31][C:32]([NH2:33])=[C:27]5[CH:26]=[N:25]4)[CH2:20][CH2:19]3)=[CH:15][CH:14]=1)=[N:8]2.Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>O>[NH2:33][C:32]1[N:31]=[CH:30][N:29]=[C:28]2[N:24]([CH:21]3[CH2:20][CH2:19][N:18]([CH2:17][C:16]4[CH:34]=[CH:35][C:13]([C:7]5[C:6]([C:36]6[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=6)=[CH:5][C:4]6[C:3](=[O:2])[NH:12][CH:11]=[CH:10][C:9]=6[N:8]=5)=[CH:14][CH:15]=4)[CH2:23][CH2:22]3)[N:25]=[CH:26][C:27]=12

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1-{1-[4-(5-methoxy-3-phenyl-1,6-naphthyridin-2-yl)benzyl]-piperidin-4-yl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine (50 mg, 0.092 mmol) and pyridine hydrochloride 9500 mg, 4.35 mmol) was heated at 150° C. for 10 minutes. The cooled mixture was diluted with water and made neutral with sodium bicarbonate solution. The white solid was collected by filtration, dried, and then digested in acetonitrile with a little methanol. Upon cooling the pure product was isolated by filtration. 1H-NMR (500 MHz, DMSO-d6): δ 11.60 (1H, br s), 8.38 (1H, s), 8.15 (1H, s), 8.07 (1H, s), 7.50 (1H, d, J=7.3 Hz), 7.31-7.60 (5H, m), 7.24-7.28 (4H, m), 6.69 (1H, d, J=7.3 Hz), 4.57 (1H, m), 3.53 (2H, s), 2.91 (2H, m), 2.11-2.17 (4H, m), 1.80-1.87 (2H, m). m/e (m+1): 529.3.

Workup

filtrationThe white solid was collected by filtration
customdried
temperatureUpon cooling the pure product
customwas isolated by filtration

Sources & evidence

ORD record: ord-0298fdda1ba34598a8fa4115a5b211f9
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910561B2

Reaction notes

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