Prolinol, (R)- → HCID 11712914, compound

HRID 550491Notes

Reaction equation

HRID 550491 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]=[C:29]([F:33])[CH:28]=3)=[C:21]([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]>>[F:33][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=1)[CH2:26][O:25][C:22]1[CH:23]=[CH:24][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:20][C:21]=1[CH3:34]

Participants

3

Reactant 2

HCID 2724541Prolinol, (R)-HCID 11525981HCID 11525981, compound

Product 1

HCID 11712914HCID 11712914, compoundYield 14%

Procedure

The procedure described in Example 55 was repeated using 2-{[4-({4-[(3-fluorobenzyl)oxy]-3-methylphenyl}amino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]oxy}ethyl methanesulfonate and (R)-2-pyrrolidinemethanol to give the title compound in 14% yield; NMR Spectrum: 1.51 (m, 1H), 1.66 (m, 2H), 1.80 (m, 1H), 2.23 (s, 3H), 2.32 (q, 1H), 2.57 (m, 1H), 2.75 (dt, 1H), 3.14 (td, 1H), 3.24 (m, 1H), 3.40 (m, 2H), 4.39 (t, 2H), 4.44 (s, 1H), 5.16 (s, 2H), 7.00 (d, 1H), 7.16 (td, 1H), 7.31 (m, 2H), 7.48 (m, 3H), 8.16 (s, 1H), 8.24 (s, 1H); Mass Spectrum: 493 (MH+).

Sources & evidence

ORD record
ord-4447f826621140f398cb6c8b236842ce
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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