Potassium Iodide → HCID 11641266, compound

HRID 550467Notes

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[CH2:41][CH2:40][O:39][CH2:38][CH2:37]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:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]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 8083Morpholine

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 11641266HCID 11641266, compoundYield 46%

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 morpholine to give the title compound in 46% yield; NMR Spectrum: 2.45 (s, 3H), 2.51 (hidden by DMSO, 4H), 2.84 (t, 2H), 3.57 (s, 4H), 4.46 (t, 2H), 7.27 (m, 3H), 7.56 (dd, 1H), 8.00 (dd, 1H), 8.24 (d, 1H), 8.36 (s, 1H), 8.62 (br s, 1H); Mass Spectrum: 466 (MH+).

Sources & evidence

ORD record: ord-bf25af26d3bf48d480d2e219b7418dab
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947676B2

Reaction notes

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