Prolinol, (R)- → HCID 11547992, compound

HRID 550477Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:14]2[C:9](=[N:10][CH:11]=[N:12][C:13]=2[NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[C:18]([Cl:30])[CH:17]=2)[NH:8][N:7]=1.[NH:31]1[CH2:35][CH2:34][CH2:33][C@@H:32]1[CH2:36][OH:37]>>[Cl:30][C:18]1[CH:17]=[C:16]([NH:15][C:13]2[N:12]=[CH:11][N:10]=[C:9]3[NH:8][N:7]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:31]4[CH2:35][CH2:34][CH2:33][C@@H:32]4[CH2:36][OH:37])[C:14]=23)[CH:21]=[CH:20][C:19]=1[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1

Participants

Reactant 2

HCID 2724541Prolinol, (R)-

HCID 11575912HCID 11575912, compound

Product 1

HCID 11547992HCID 11547992, compoundYield 14%

Procedure

The procedure described in Example 23 was repeated using 3-(3-chloropropoxy)-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine and (R)-2-pyrrolidinemethanol to give the title compound in 14% yield; NMR Spectrum (DMSO+TFA): 1.77-1.81 (m, 1H), 1.89-1.93 (m, 1H), 1.99-2.04 (m, 1H), 2.09-2.14 (m, 1H), 2.25 (br s, 2H), 3.14-3.19 (m, 1H), 3.26 (br s, 1H), 3.58-3.65 (m, 4H), 3.76-3.79 (m, 1H), 4.48 (br s, 2H), 5.62 (s, 2H), 7.45 (d, 1H), 7.56 (d, 1H), 7.80 (s, 1H), 7.98 (t, 1H), 8.12 (d, 1H), 8.40 (s, 1H), 8.55 (t, 1H), 8.98 (d, 1H); Mass Spectrum: 510 (MH+).

Sources & evidence

ORD record: ord-9a5f31065332450b9395b34e86b91127
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947676B2

Reaction notes

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