Benzenesulfonyl chloride → N-{7-[(2-Morpholin-4-ylethyl)amino]-1-benzofuran-5-yl}benzenesulfonamide hydrochloride

HRID 1162003Notes

Reaction equation

HRID 1162003 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[C:18]3[O:17][CH:16]=[CH:15][C:14]=3[CH:13]=[C:12]([NH2:19])[CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:27]1([S:33]([Cl:36])(=[O:35])=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl>[ClH:36].[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[C:18]3[O:17][CH:16]=[CH:15][C:14]=3[CH:13]=[C:12]([NH:19][S:33]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:35])=[O:34])[CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 86058078N7-(2-Morpholin-4-ylethyl)-1-benzofuran-5,7-diamine2×

Product 1

HCID 66892999N-{7-[(2-Morpholin-4-ylethyl)amino]-1-benzofuran-5-yl}benzenesulfonamide hydrochlorideYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N7-(2-Morpholin-4-ylethyl)-1-benzofuran-5,7-diamine (58 mg, 0.221 mmol; Intermediate 28) in dichloromethane (2 mL) were added triethylamine (62 μL, 0.442 mmol) and benzenesulfonyl chloride (39 mg, 0.221 mmol). The mixture was stirred at room temperature for 1 h and evaporated. The residue was purified by preparative HPLC (System D), evaporated pure fractions, and converted the resulting TFA salt to a HCl salt. Yield: 32%, HPLC purity=100%, m/z=402 (M+H)+, 1H NMR (270 MHz, methanol-d4) δ ppm 3.43 (t, J=6.06 Hz, 2H) 3.40-3.61 (m, J=6.06, 6.06 Hz, 4H) 3.68 (t, J=6.06 Hz, 2H) 3.75-4.14 (m, 4H) 6.48-6.55 (m, 2H) 6.64 (d, J=2.23 Hz, 1H) 7.41-7.59 (m, 3H) 7.65-7.74 (m, 3H).

Workup

  1. customevaporated
  2. customThe residue was purified by preparative HPLC (System D)
  3. customevaporated pure fractions

Sources & evidence

ORD record
ord-1c4b31394d3d45989a644b27502e5b61
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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