(3S)-pyrrolidin-3-ol → HCID 67020572, compound

HRID 550456Notes

Reaction equation

HRID 550456 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]([CH3:29])[CH:16]=2)[NH:7][N:6]=1.[NH:30]1[CH2:34][CH2:33][C@H:32]([OH:35])[CH2:31]1>>[CH3:29][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][C@H:32]([OH:35])[CH2:31]4)[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 2733874(3S)-pyrrolidin-3-olHCID 11611268HCID 11611268, compound

Product 1

HCID 67020572HCID 67020572, compoundYield 15%

Procedure

The procedure described in Example 23 was repeated using 3-(2-chloroethoxy)-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine and (S)-3-pyrrolidinol to give the title compound in 15% yield; N Spectrum: 1.50-1.55 (m, 1H), 1.91-1.96 (m, 1H), 2.19 (s, 3H), 2.41-2.44 (m, 1H), 2.44 (s, 3H), 2.55 (dd, 1H), 2.68 (dd, 1H), 2.82-2.90 (m, 3H), 4.17 (br s, 1H), 4.41 (t, 2H), 4.70 (br s, 1H), 6.95 (d, 1H), 7.17-7.25 (m, 2H), 7.62-7.65 (m, 2H), 8.16 (s, 1H), 8.30 (s, 1H), 8.34 (s, 1H); Mass Spectrum: 462 (MH+).

Sources & evidence

ORD record
ord-1aa331a780b44c26ab9ee2836532ff06
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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