Pyridine → HCID 66799985, compound

HRID 589787Notes

Reaction equation

N[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH:12]([C:15]1[CH:16]=[CH:17][C:18]2[O:22][C:21]([S:23](Cl)(=[O:25])=[O:24])=[C:20]([CH3:27])[C:19]=2[CH:28]=1)([CH3:14])[CH3:13].[N:29]1C=CC=CC=1.C(O)(C(F)(F)F)=O>CC#N.CO.O>[CH3:27][C:20]1[C:19]2[CH:28]=[C:15]([CH:12]([CH3:14])[CH3:13])[CH:16]=[CH:17][C:18]=2[O:22][C:21]=1[S:23]([NH:29][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:2]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:25])=[O:24]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of methyl 4-aminobenzoate (16 mg, 0.106 mmol), 5-isopropyl-3-methylbenzofuran-2-sulfonyl chloride (Intermediate 16) (40 mg, 0.147 mmol) and pyridine (20 μL, 0.25 mmol) in MeCN (600 μL) was stirred at 50° C. over night. The reaction mixture was diluted with MeOH/water and acidified by addition of TFA. The crude product was purified by reversed phase chromatography (ACE C8, 5 μm, 21×50 mm, flow 25 ml/min, 0.1% TFA in water/MeCN over 6 minutes). The title compound was obtained in 17% yield (6.7 mg). 1H NMR (500 MHz, MeOH-d4) δ ppm 1.28 (d, J=6.96 Hz, 6 H) 2.41 (s, 3 H) 3.02 (spt, J=6.96 Hz, 1 H) 3.85 (s, 3 H) 7.31-7.37 (m, 2 H) 7.37 (dd, J=8.67, 1.68 Hz, 1 H) 7.40 (dd, J=8.67, 0.75 Hz, 1 H) 7.46 (dt, J=1.68, 0.75 Hz, 1 H) 7.69-7.73 (m, 1 H) 7.82-7.84 (m, 1H). MS (ESI+) m/z 388 [M+H]+.

Workup

customThe crude product was purified by reversed phase chromatography (ACE C8, 5 μm, 21×50 mm, flow 25 ml/min, 0.1% TFA in water/MeCN over 6 minutes)

Sources & evidence

ORD record: ord-cc0174ef1dcc4c6e9485ab012a6ea2fb
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233946B2

Reaction notes

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