Pyridine → N-(7-Pyrimidin-5-yl-1-benzofuran-5-yl)benzenesulfonamide hydrochloride

HRID 1161987Notes

Reaction equation

HRID 1161987 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.[N:17]1[CH:22]=[C:21]([C:23]2[C:31]3[O:30][CH:29]=[CH:28][C:27]=3[CH:26]=[C:25]([NH2:32])[CH:24]=2)[CH:20]=[N:19][CH:18]=1>ClCCl>[ClH:10].[N:17]1[CH:22]=[C:21]([C:23]2[C:31]3[O:30][CH:29]=[CH:28][C:27]=3[CH:26]=[C:25]([NH:32][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[CH:24]=2)[CH:20]=[N:19][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 668929957-Pyrimidin-5-yl-1-benzofuran-5-amine2×

Product 1

HCID 66891388N-(7-Pyrimidin-5-yl-1-benzofuran-5-yl)benzenesulfonamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzenesulfonyl chloride (0.093 g, 0.524 mmol) and pyridine (347 μL, 430 mmol) were added to 7-pyrimidin-5-yl-1-benzofuran-5-amine (0.100 g, 0.473 mmol; Intermediate 18) in dichloromethane (2 mL). The mixture was shaken at room temperature for 1 h and the solvent was removed. The crude product was purified by preparative HPLC using acetonitrile-water gradients containing 0.1% trifluoroacetic acid and then converted into the hydrochloride salt by treatment with 2 M HCL in diethyl ether. This gave 0.071 g (43%) of the title compound as a yellow solid. HPLC 97%, RT: 1.863 min (System A; 10-97% over 3 min). 1H NMR (500 MHz, DMSO-d6) δ ppm 6.98 (d, J=2.20 Hz, 1H) 7.34 (d, J=2.20 Hz, 1H) 7.50-7.54 (m, 3H) 7.58-7.60 (m, 1H) 7.80-7.82 (m, 1H) 7.97 (d, J=2.20 Hz, 1H) 9.10 (s, 2H) 9.20 (s, 1H) 9.87 (s, 1H). GC-MS 351 (M+).

Workup

  1. customthe solvent was removed
  2. customThe crude product was purified by preparative HPLC
  3. additioncontaining 0.1% trifluoroacetic acid
  4. wait10-97% over 3 min)

Sources & evidence

ORD record
ord-3050930a6ec74245b2226e3557ea3dd8
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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