Pyridine → N-[7-(Pyridin-4-ylamino)-1-benzofuran-5-yl]benzenesulfonamide hydrochloride

HRID 1162006Notes

Reaction equation

[C:1]1([S:7]([Cl:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[NH2:17][C:18]1[CH:19]=[C:20]([NH:27][C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)[C:21]2[O:25][CH:24]=[CH:23][C:22]=2[CH:26]=1>C(Cl)Cl>[ClH:10].[N:31]1[CH:32]=[CH:33][C:28]([NH:27][C:20]2[C:21]3[O:25][CH:24]=[CH:23][C:22]=3[CH:26]=[C:18]([NH:17][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[CH:19]=2)=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Benzenesulfonyl chloride (65 μL, 0.48 mmol) and pyridine (289 μL, 3.58 mmol) were added to (5-amino-1-benzofuran-7-yl)pyridin-4-yl-amine (90 mg, 0.40 mmol; Intermediate 33) in DCM (2 mL). The mixture was heated at 40° C. for 10 min, shaken at room temperature for 1 h, and solvent was removed in vacuo. The residue was purified by preparative HPLC using acetonitrile-water gradients containing 0.1% trifluoroacetic acid. The obtained TFA salt was converted into the hydrochloride salt by treatment with 2 M HCl in ether to afford 78.7 mg (45%) of the title product. HPLC 100%, RT: 1.560 (System A; 10-97% MeCN over 3 min). 1H NMR (270 MHz, methanol-d4) δ ppm 6.91 (s, 1H) 7.04 (d, J=2.23 Hz, 2H) 7.36 (d, J=1.98 Hz, 1H) 7.51-7.65 (m, 3H) 7.74-7.77 (m, 2H) 8.03 (d, J=1.98 Hz, 1H) 8.32 (d, J=6.93 Hz, 2H) 10.43 (s, 1H) 10.84 (s, 1H). LC-MS 366 (M+H)+.

Workup

customsolvent was removed in vacuo
customThe residue was purified by preparative HPLC
additioncontaining 0.1% trifluoroacetic acid

Sources & evidence

ORD record: ord-affdcad7d116441782bc3f17885c678e
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820675B2

Reaction notes

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