Methyl iodide → HCID 86659294, compound

HRID 1806077Notes

Reaction equation

[ClH:1].Cl.[CH3:3][C:4]1[N:5]=[C:6]([NH:9][C:10]2[N:15]=[CH:14][C:13]([S:16][CH2:17][C:18]3[C:23]([OH:24])=[CH:22][CH:21]=[CH:20][N:19]=3)=[CH:12][C:11]=2[O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[S:7][CH:8]=1.[H-].[Na+].[CH3:34]I>CN(C=O)C>[ClH:1].[CH3:34][O:24][C:23]1[C:18]([CH2:17][S:16][C:13]2[CH:12]=[C:11]([O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:10]([NH:9][C:6]3[S:7][CH:8]=[C:4]([CH3:3])[N:5]=3)=[N:15][CH:14]=2)=[N:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Placed 2-((6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)methyl)pyridine-3-ol (prepared in Example 69) (0.180 g, 0.426 mmol) in DMF (5 mL) and cooled to 0° C. Sodium hydride (0.0307 g, 1.28 mmol) was added and stirred for 10 minutes then MeI (0.0605 g, 0.426 mmol) was added stirred at ambient temperature for 30 minutes. Added water and extracted with CH2Cl2. The organic layer was concentrated and purified by silica gel. The product was still impure. Mixture was purified by medium pressure reverse phase followed by two high pressure reverse phase purifications. Combined all clean fractions then dissolved in CH2Cl2 and added HCl in ether, then concentrated to give the title compound (0.0085 g, 4.22% yield). 1H NMR (d6-DMSO) δ 8.14 (m, 1H), 8.10 (d, 1H), 7.65 (m, 1H), 7.55 (m, 1H), 7.34-7.27 (m, 3H), 7.03 (m, 1H), 6.85 (d, 2H), 6.36 (s, 1H), 4.24 (s, 2H), 3.17 (s, 3H), 2.18 (s, 3H).

Workup

stirringstirred at ambient temperature for 30 minutes
extractionAdded water and extracted with CH2Cl2
concentrationThe organic layer was concentrated
custompurified by silica gel
customMixture was purified by medium pressure
dissolutionthen dissolved in CH2Cl2
additionadded HCl in ether
concentrationconcentrated

Sources & evidence

ORD record: ord-3b66e434901448fd845ccbb3a7fe332f
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354540B2

Reaction notes

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