HCID 58268353, compound → HCID 44178160, compound

HRID 1898292Notes

Reaction equation

C([Si](C)(C)[N:6]1[C:10]2[N:11]=[CH:12][CH:13]=[C:14]([C:15]([C:17]3[C:22]([N:23](COC)[S:24]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([C:34]([F:37])([F:36])[F:35])[CH:28]=4)(=[O:26])=[O:25])=[CH:21][C:20]([Cl:41])=[C:19]([CH3:42])[N:18]=3)=[O:16])[C:9]=2[CH:8]=[CH:7]1)(C)(C)C>Cl.O1CCOCC1>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([S:24]([NH:23][C:22]2[C:17]([C:15]([C:14]3[C:9]4[CH:8]=[CH:7][NH:6][C:10]=4[N:11]=[CH:12][CH:13]=3)=[O:16])=[N:18][C:19]([CH3:42])=[C:20]([Cl:41])[CH:21]=2)(=[O:25])=[O:26])=[CH:28][C:29]=1[C:34]([F:37])([F:36])[F:35]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of N-{2-[1-(tert-Butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonyl]-5-chloro-6-methyl-pyridin-3-yl}-4-chloro-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (from above step) in 2 ml of 4M HCl and 2 ml of dioxane was stirred at 90° C. for 2 hours. The mixture was concentrated and the residue was diluted with ethyl acetate, this organic layer was washed with saturated sodium bicarbonate and followed by brine and then dried over sodium sulfate. After filtration and concentration the residue was purified by preparative TLC to afford the title compound. 1H NMR: (CD3OD, ppm): 8.15 (d, 1H), 7.98 (s, 1H), 7.84 (m, 1H), 7.53 (m, 1H), 7.40 (d, 1H), 7.26 (d, 1H), 7.07 (d, 1H), 6.23 (d, 1H), 2.47 (s, 3H); MS (ES) (M++H) expect 529. found 528.9

Workup

concentrationThe mixture was concentrated
additionthe residue was diluted with ethyl acetate
washthis organic layer was washed with saturated sodium bicarbonate
dry with materialdried over sodium sulfate
filtrationAfter filtration and concentration the residue
customwas purified by preparative TLC

Sources & evidence

ORD record: ord-4118b1f6a8bd4f0a945fc5f4731d2772
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08519135B2

Reaction notes

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