Prolinol, (R)- → HCID 11627593, compound

HRID 550489Notes

Reaction equation

HRID 550489 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]([O:34][CH3:35])[CH:20]=2)[NH:11][N:10]=1)(=O)=O.[NH:36]1[CH2:40][CH2:39][CH2:38][C@@H:37]1[CH2:41][OH:42]>>[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:36]4[CH2:40][CH2:39][CH2:38][C@@H:37]4[CH2:41][OH:42])[C:17]=23)=[CH:20][C:21]=1[O:34][CH3:35]

Participants

3

Reactant 2

HCID 2724541Prolinol, (R)-HCID 11555176HCID 11555176, compound

Product 1

HCID 11627593HCID 11627593, compoundYield 37%

Procedure

The procedure described in Example 55 was repeated using 2-{[4-({4-[(3-fluorobenzyl)oxy]-3-methoxyphenyl}amino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]oxy}ethyl methanesulfonate and (R)-2-pyrrolidinemethanol to give the title compound in 37% yield; NMR Spectrum: 1.50 (m, 1H), 1.64 (m, 2H), 1.80 (m, 1H), 2.32 (q, 1H), 2.59 (m, 1H), 2.78 (dt, 1H), 3.15 (t, 1H), 3.27 (m, 3H), 3.80 (s, 3H), 4.37 (hidden by water, 2H), 4.40 (t, 1H), 4.46 (s, 1H), 5.11 (s, 2H), 7.02 (d, 1H), 7.16 (t, 2H), 7.28 (td, 2H), 7.38 (d, 1H), 7.44 (q, 1H), 8.27 (d, 2H), 8.29 (s, 1H); Mass Spectrum: 509 (MH+).

Sources & evidence

ORD record
ord-a6c5507194ce438cbcdc4e8508b6f793
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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