Prolinol, (R)- → HCID 67020864, compound

HRID 550510Notes

Reaction equation

HRID 550510 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][C:22]3[CH:23]=[N:24][C:25]([CH3:28])=[CH:26][CH:27]=3)=[C:17]([Cl:29])[CH:16]=2)[NH:7][N:6]=1.[NH:30]1[CH2:34][CH2:33][CH2:32][C@@H:31]1[CH2:35][OH:36]>>[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:30]4[CH2:34][CH2:33][CH2:32][C@@H:31]4[CH2:35][OH:36])[C:13]=23)[CH:20]=[CH:19][C:18]=1[O:21][C:22]1[CH:23]=[N:24][C:25]([CH3:28])=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 2724541Prolinol, (R)-HCID 116548903-(2-chloroethoxy)-N-{3-chloro-4-[(6-methylpyridin-3-yl)oxy]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 67020864HCID 67020864, compoundYield 45%

Procedure

The procedure described in Example 23 was repeated using 3-(2-chloroethoxy)-N-{3-chloro-4-[(6-methylpyridin-3-yl)oxy]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine (prepared as described in Example 16) and (R)-2-pyrrolidinemethanol to give the title compound in 45% yield; NMR Spectrum: 1.50-1.81 (m, 4H), 2.33 (dd, 1H), 2.45 (s, 3H), 2.58 (m, 1H), 2.74-2.79 (m, 1H), 3.11-3.19 (m, 1H), 3.24-3.32 (m, 3H), 4.44 (t, 2H), 7.20 (d, 1H), 7.27 (br s, 2H), 7.73 (d, 1H), 8.14 (s, 1H), 8.21 (s, 1H), 8.36 (s, 1H), 8.62 (br s, 1H); Mass Spectrum: 496 (MH+).

Sources & evidence

ORD record
ord-57308b29ae464c95982929f73ac3433f
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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