Benzenesulfonamide → HCID 10099209, compound

HRID 860035Notes

Reaction equation

HRID 860035 reaction equation
[C:1]([C:4]1[O:5][C:6]2[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]([N:15]([C:23]3[CH:28]=[CH:27][C:26]([C:29](O)=[O:30])=[CH:25][CH:24]=3)[CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[C:7]=2[CH:8]=1)(=[O:3])[CH3:2].[C:32]1([S:38]([NH2:41])(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.ClCCl>[C:1]([C:4]1[O:5][C:6]2[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]([N:15]([C:23]3[CH:24]=[CH:25][C:26]([C:29]([NH:41][S:38]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)(=[O:40])=[O:39])=[O:30])=[CH:27][CH:28]=3)[CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[C:7]=2[CH:8]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 7370BenzenesulfonamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 10364586HCID 10364586, compound

Product 1

HCID 10099209HCID 10099209, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-acetyl-7-methoxy-N-(4-carboxyphenyl)-N-(3-pyridylmethyl)-4-aminobenzofuran (416 mg, 1.0 mmol), benzenesulfonamide (200 mg, 1.2 mmol), and DMAP (150 mg, 1.2 mmol) in dichloromethane (5 mL) at room temperature was added EDCI (230 mg, 1.2 mmol) in one portion and the mixture was stirred at room temperature for 16 h. The mixture was partitioned between water (25 mL) and EtOAc (25 mL) and the pH was adjusted to 5–6 with 1.0N HCl. The EtOAc was separated, washed with brine (25 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography eluting with a linear gradient from 5% to 10% MeOH in EtOAc to give 2-Acetyl-7-methoxy-N-(4-phenylsulfonylaminocarbonylphenyl)-N-(3-pyridylmethyl)-4-aminobenzofuran (415 mg). 1H NMR (300 MHz) δ 8.53 (br,1H), 8.46 (br,1H), 8.06 (d,J=7.3 Hz,2H), 7.8–7.3 (m,6H), 7.21 (m,1H), 7.1–7.0 (m,2H), 6.91 (d,J=8.5 Hz,1H), 6.56 (d,J=7.3 Hz,2H), 4.99 (s,2H), 4.02 (s,3H), 2.54 (s,3H).

Workup

  1. customThe mixture was partitioned between water (25 mL) and EtOAc (25 mL)
  2. customThe EtOAc was separated
  3. washwashed with brine (25 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. washeluting with a linear gradient from 5% to 10% MeOH in EtOAc

Sources & evidence

ORD record
ord-89d06118173143cca48ff505c709c392
Source dataset
uspto-grants-2006_12
Patent number
US07153871B2

Reaction notes

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