Potassium Iodide → HCID 11712708, compound

HRID 550463Notes

Reaction equation

[I-].[K+].CS(O[CH2:8][CH2:9][O:10][C:11]1[C:19]2[C:14](=[N:15][CH:16]=[N:17][C:18]=2[NH:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]3[CH:29]=[N:30][C:31]([CH3:34])=[CH:32][CH:33]=3)=[C:23]([F:35])[CH:22]=2)[NH:13][N:12]=1)(=O)=O.[NH:36]1[CH2:40][CH2:39][CH2:38][C@@H:37]1[CH2:41][OH:42]>>[F:35][C:23]1[CH:22]=[C:21]([NH:20][C:18]2[N:17]=[CH:16][N:15]=[C:14]3[NH:13][N:12]=[C:11]([O:10][CH2:9][CH2:8][N:36]4[CH2:40][CH2:39][CH2:38][C@@H:37]4[CH2:41][OH:42])[C:19]=23)[CH:26]=[CH:25][C:24]=1[O:27][C:28]1[CH:29]=[N:30][C:31]([CH3:34])=[CH:32][CH:33]=1

Participants

Reactant 3

HCID 4875Potassium Iodide

HCID 2724541Prolinol, (R)-

HCID 11719830Ethanol, 2-[[4-[[3-fluoro-4-[(6-methyl-3-pyridinyl)oxy]phenyl]amino]-1H-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]-, 1-methanesulfonate

Product 1

HCID 11712708HCID 11712708, compoundYield 30%

Procedure

The procedure described in Example 23 was repeated (except that potassium iodide was not used) using 2-{[4-({3-fluoro-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]oxy}ethyl methanesulfonate (prepared as described in Example 20) and (R)-2-pyrrolidinemethanol to give the title compound in 30% yield; NMR Spectrum: 1.51 (m, 1H), 1.65 (m, 2H), 1.80 (m, 1H), 2.33 (q, 1H), 2.45 (s, 3H), 2.57 (m, 1H), 2.78 (dt, 1H), 3.14 (t, 1H), 3.28 (hidden by DMSO, 2H), 4.41 (t, 2H), 4.47 (br s, 1H), 7.25 (m, 3H), 7.56 (d, 1H), 7.85 (td, 1H), 8.01 (dd, 1H), 8.24 (d, 1H), 8.37 (s, 1H), 8.59 (br s, 1H); Mass Spectrum: 480 (MH+).

Sources & evidence

ORD record: ord-157801aa54e64688b3c25ba845574cdf
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947676B2

Reaction notes

Loading…