4-Methoxypiperidine → N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-3-[2-(4-methoxypiperidin-1-yl)ethoxy]-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 550524Notes

Reaction equation

HRID 550524 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][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[C:17]([Cl:29])[CH:16]=2)[NH:7][N:6]=1.[CH3:30][O:31][CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]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:35]4[CH2:36][CH2:37][CH:32]([O:31][CH3:30])[CH2:33][CH2:34]4)[C:13]=23)[CH:20]=[CH:19][C:18]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1

Participants

3

Reactant 2

HCID 776664-MethoxypiperidineHCID 115028913-(2-chloroethoxy)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 44455195N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-3-[2-(4-methoxypiperidin-1-yl)ethoxy]-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 35%

Procedure

The procedure described in Example 23 was repeated using 3-(2-chloroethoxy)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (prepared as described in Example 13) and 4-methoxypiperidine (prepared as described in Example 118, starting material) to give the title compound in 35% yield; NMR Spectrum: 1.35-1.42 (m, 2H), 1.78-1.80 (m, 2H), 2.18-2.22 (m, 2H), 2.77-2.79 (m, 4H), 3.11-3.16 (m, 1H), 3.20 (s, 3H), 4.40 (t, 2H), 5.29 (s, 2H), 7.24 (d, 1H), 7.36-7.38 (m, 1H), 7.55-7.58 (m, 2H), 7.86-7.90 (m, 2H), 8.29 (s, 1H), 8.50 (s, 1H), 8.59 (d, 1H); Mass Spectrum: 510 (MH+).

Sources & evidence

ORD record
ord-d571b3213a854f3fb978693445f58f75
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

Loading…