HCID 57942109, compound → HCID 57942325, compound

HRID 419200Notes

Reaction equation

C([Si](C)(C)[O:6][CH2:7][CH2:8][NH:9][C:10]1[CH:15]=[C:14]([CH:16]([OH:39])[C:17]2[C:22]([NH:23][S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([C:34]([F:37])([F:36])[F:35])[CH:28]=3)(=[O:26])=[O:25])=[CH:21][C:20]([Cl:38])=[CH:19][N:18]=2)[CH:13]=[CH:12][N:11]=1)(C)(C)C>O=[Mn]=O.O1CCOCC1>[Cl:38][C:20]1[CH:21]=[C:22]([NH:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([C:34]([F:35])([F:36])[F:37])[CH:28]=2)(=[O:26])=[O:25])[C:17]([C:16]([C:14]2[CH:13]=[CH:12][N:11]=[C:10]([NH:9][CH2:8][CH2:7][OH:6])[CH:15]=2)=[O:39])=[N:18][CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To the dioxane (1 mL) solution of N-[2-({2-[2-(tert-butyl-dimethyl-silanyloxy)-ethylamino]-pyridin-4-yl}-hydroxy-methyl)-5-chloro-pyridin-3-yl]-4-methyl-3-trifluoromethyl-benzenesulfonamide from step 1, was added MnO2 (440 mg, 5 mmol). The mixture was stirred at 80° C. for 1 hour, filtered, concentrated. The deprotection was performed in 4 M HCl in dioxane (4 mL) and water (1 mL) for 1 hour at RT. The solvent was evaporated and the residue was purified with HPLC to give N-{5-chloro-2-[2-(2-hydroxy-ethylamino)-pyridine-4-carbonyl]-pyridin-3-yl}-4-methyl-3-trifluoromethyl-benzenesulfonamide: 1H NMR (400 MHz, CDCl3) δ 8.3 (s, 1H), 8.15 (d, 2H), 8.05 (s, 1H), 7.9 (d, 1H), 7.4 (d, 1H), 6.7 (m, 2H), 3.8 (m, 2H), 3.5 (m, 2H), 2.5 (s, 3H); MS m/z: 515 (M+H)+.

Workup

filtrationfiltered
concentrationconcentrated
waitwater (1 mL) for 1 hour at RT
customThe solvent was evaporated
customthe residue was purified with HPLC

Sources & evidence

ORD record: ord-99889ed1485f484298b11fa869d7b083
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093247B2

Reaction notes

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