Benzenesulfonyl chloride → HCID 66893753, compound

HRID 1162012Notes

Reaction equation

HRID 1162012 reaction equation
[C:1]1([S:7]([Cl:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:11]1([CH2:16][CH2:17][NH:18][C:19]2[C:27]3[O:26][CH:25]=[CH:24][C:23]=3[CH:22]=[C:21]([NH2:28])[CH:20]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1.C(N(CC)CC)C>ClCCl>[ClH:10].[N:11]1([CH2:16][CH2:17][NH:18][C:19]2[C:27]3[O:26][CH:25]=[CH:24][C:23]=3[CH:22]=[C:21]([NH:28][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[CH:20]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 86057984HCID 86057984, compound

Product 1

HCID 66893753HCID 66893753, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a test tube containing benzenesulfonyl chloride (42 mg, 0.235 mmol) was added a solution of N7-(2-pyrrolidin-1-ylethyl)-1-benzofuran-5,7-diamine* (48 mg, 0.195 mmol) in dichloromethane (3 mL). After addition of triethylamine (55 μl, 0.391 mmol), the mixture was shaken for 1 h and then concentrated. The residue was purified by preparative HPLC. The resulting TFA-salt was treated with HCl/ether and evaporated to provide the title compound. Yield: 5%, HPLC purity=99%, m/z=386 (M+H)+, 1H NMR (270 MHz, methanol-d4) δ ppm 1.95-2.26 (m, 4H) 3.03-3.24 (m, 2H) 3.38-3.47 (m, 2H) 3.58-3.65 (m, 2H) 3.64-3.77 (m, 2H) 6.45-6.48 (m, 1H) 6.55-6.57 (m, 1H) 6.65 (d, J=2.23 Hz, 1H) 7.40-7.59 (m, 3H) 7.67 (d, J=2.23 Hz, 1H) 7.68-7.73 (m, 2H). *Prepared in two steps starting from 2-pyrrolidin-1-yl-ethylamine: i) Pd-catalysed amination of 7-iodo-5-nitro-benzofuran according to the procedure of Intermediate 31 to provide (5-nitro-benzofuran-7-yl)-(2-pyrrolidin-1-yl-ethyl)-amine and ii) reduction of the nitro group of (5-nitro-benzofuran-7-yl)-(2-pyrrolidin-1-yl-ethyl)-amine to provide N7-(2-pyrrolidin-1-ylethyl)-1-benzofuran-5,7-diamine according to the procedure of Example 48 (Step 1).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by preparative HPLC
  3. additionThe resulting TFA-salt was treated with HCl/ether
  4. customevaporated

Sources & evidence

ORD record
ord-512e79ea515d491ebc9a9b11647e13ff
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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