Hydrochloric Acid → HCID 21099433, compound

HRID 2376962Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=2[C:22]#[N:23])(=[O:19])=[O:18])=[CH:13][CH:12]=1.[OH-:28].[Na+].O.Cl>C(O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:12]=[CH:13][C:14]([S:17]([C:20]2[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=2[C:22]([NH2:23])=[O:28])(=[O:18])=[O:19])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 78 °C

Procedure

2-({4-[(E)-2-(2,4-Difluorophenyl)vinyl]phenyl}sulfonyl)benzonitrile (Example 47, 100 mg, 0.26 mmol) was dissolved in ethanol (0.26 mL) and 4N sodium hydroxide (0.11 mL, 0.26 mmol) was added. The reaction was heated to 78° C. for 12 hours. After cooling, water and ethyl acetate were added. The aqueous layer was acidified with HCl and extracted with ethyl acetate (×2). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with ethyl acetate, to yield the title compound as a white solid (54 mg, 52%). δH (400 MHz, d6 DMSO): 8.09 (1H, dd, J=0.9, 7.8 Hz), 7.99 (2H, d, J=8.5 Hz), 7.95 (1H, s), 7.86 (1H, q, J=8.2 Hz), 7.80 (2H, d, J=8.5 Hz), 7.74-7.62 (2H, m), 7.58 (1H, s), 7.47-7.27 (4H, m), 7.15 (1H, td, J=1.7, 8.5 Hz); m/z (ES+) 400 [MH+], 383 [(MH+)−17].

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate (×2)
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-1253b3efcec24ff98bbef17c417d9329
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468393B2

Reaction notes

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