Potassium Iodide → HCID 11670167, compound

HRID 550466Notes

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.[OH:36][CH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1>>[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:40]4[CH2:41][CH2:42][CH:37]([OH:36])[CH2:38][CH2:39]4)[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 79341Piperidin-4-ol

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 11670167HCID 11670167, compoundYield 39%

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 and 4-hydroxypiperidine to give the title compound in 39% yield; NMR Spectrum: 1.37 (m, 1H), 1.67 (d, 1H), 2.16 (t, 1H), 2.45 (s, 3H), 2.78 (t, 2H), 4.42 (t, 2H), 4.54 (d, 1H), 7.23 (m, 3H), 7.56 (dd, 1H), 8.01 (dd, 1H), 8.24 (d, 1H), 8.36 (s, 1H), 8.66 (br s, 1H); Mass Spectrum: 480 (MH+).

Sources & evidence

ORD record: ord-4054399a890b48a486f959d374ed53d7
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947676B2

Reaction notes

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