2-(Methylamino)ethanol → 2-[{2-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl}(methyl)amino]ethanol

HRID 550435Notes

Reaction equation

HRID 550435 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][NH:31][CH2:32][CH2:33][OH:34]>>[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:31]([CH3:30])[CH2:32][CH2:33][OH:34])[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 80162-(Methylamino)ethanolHCID 115028913-(2-chloroethoxy)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 115618542-[{2-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl}(methyl)amino]ethanolYield 44%

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 and N-methylethanolamine to give the title compound in 44% yield; NMR Spectrum: 2.30 (s, 3H), 2.52-2.55 (m, 2H), 2.88 (t, 2H), 3.47-3.50 (m, 2H), 4.39 (t, 2H), 5.28 (s, 2H), 7.25 (d, 1H), 7.35-7.38 (m, 1H), 7.55-7.58 (m, 2H), 7.87 (t, 1H), 7.93 (d, 1H), 8.29 (s, 1H), 8.44 (s, 1H), 8.59 (d, 1H); Mass Spectrum: 470 (MH+).

Sources & evidence

ORD record
ord-d479c72e6d00451599585a2f627ebf2b
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

Loading…