Prolinol, (R)- → ((2R)-1-{2-[(4-{[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl}pyrrolidin-2-yl)methanol

HRID 550485Notes

Reaction equation

CS(O[CH2:6][CH2:7][O:8][C:9]1[C:17]2[C:12](=[N:13][CH:14]=[N:15][C:16]=2[NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[C:21]([O:33][CH3:34])[CH:20]=2)[NH:11][N:10]=1)(=O)=O.[NH:35]1[CH2:39][CH2:38][CH2:37][C@@H:36]1[CH2:40][OH:41]>>[CH3:34][O:33][C:21]1[CH:20]=[C:19]([NH:18][C:16]2[N:15]=[CH:14][N:13]=[C:12]3[NH:11][N:10]=[C:9]([O:8][CH2:7][CH2:6][N:35]4[CH2:39][CH2:38][CH2:37][C@@H:36]4[CH2:40][OH:41])[C:17]=23)[CH:24]=[CH:23][C:22]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1

Participants

Reactant 2

HCID 2724541Prolinol, (R)-

HCID 115114392-[(4-{[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl methanesulfonate

Product 1

HCID 11663197((2R)-1-{2-[(4-{[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl}pyrrolidin-2-yl)methanolYield 47%

Procedure

The procedure described in Example 55 was repeated using 2-[(4-{[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl methanesulfonate and (R)-2-pyrrolidinemethanol to give the title compound in 47% yield; NMR Spectrum: 1.50 (m, 1H), 1.65 (m, 2H), 1.79 (m, 1H), 2.33 (q, 1H), 2.58 (m, 1H), 2.79 (dt, 1H), 3.15 (td, 1H), 3.27 (m, 1H), 3.41 (m, 1H), 3.81 (s, 3H), 4.40 (t, 2H), 4.43 (t, 1H), 5.16 (s, 2H), 7.00 (d, 1H), 7.27 (dd, 1H), 7.36 (m, 2H), 7.39 (d, 1H), 7.55 (d, 1H), 7.85 (td, 1H), 8.21 (s, 1H), 8.26 (s, 1H), 8.58 (d, 1H); Mass Spectrum: 492 (MH+).

Sources & evidence

ORD record: ord-ce09c9051f494f6abd29c016b1edd012
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947676B2

Reaction notes

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