4-acetyl-N-[3-(4-methylpiperazin-1-yl)propyl]benzenesulfonamide → 4-[3E-(2,4-Dimethoxy-5-pyrrolidin-1-ylphenyl)acryloyl]-N-[3-(4-methyl-piperazin-1-yl)propyl]benzenesulfonamide

HRID 347378Notes

Reaction equation

HRID 347378 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:24][O:25][C:26]1[CH:33]=[C:32]([O:34][CH3:35])[C:31]([N:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)=[CH:30][C:27]=1[CH:28]=O.C[O-].[Li+]>CN(C=O)C.CO>[CH3:24][O:25][C:26]1[CH:33]=[C:32]([O:34][CH3:35])[C:31]([N:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)=[CH:30][C:27]=1/[CH:28]=[CH:2]/[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]2)(=[O:11])=[O:12])=[CH:6][CH:5]=1)=[O:3]

Participants

6

Reactant 3

HCID 37907214-acetyl-N-[3-(4-methylpiperazin-1-yl)propyl]benzenesulfonamideHCID 4177230Lithium methanolateHCID 210825102,4-Dimethoxy-5-pyrrolidin-1-ylbenzaldehyde

Product 1

HCID 114443164-[3E-(2,4-Dimethoxy-5-pyrrolidin-1-ylphenyl)acryloyl]-N-[3-(4-methyl-piperazin-1-yl)propyl]benzenesulfonamideYield 57%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution 4-acetyl-N-[3-(4-methylpiperazin-1-yl)propyl]benzenesulfonamide (Ex-55A, 830 mg, 2.44 mmol) and 2,4-dimethoxy-5-pyrrolidin-1-ylbenzaldehyde (Ex-38B, 575 mg, 2.44 mmol) in DMF (10.8 mL) and MeOH (4.4 mL) was treated with lithium methoxide (278 mg, 7.32 mmol) and stirred for 20 h at room temperature under nitrogen atmosphere. The reaction mixture was quenched with water (75 mL) and extracted ethyl acetate (3×50 mL). The combined organic phase was brined, dried over sodium sulfate, and concentrated to a red solid. Column chromatography (5% MeOH in dichloromethane) gave 772 mg (57%) of the title compound as a brown solid, mp 64–68° C. 1H-NMR (300 MHz, DMSO-d6) 8.23 (d, 2H, J=8.7), 8.05 (d, 1H, J=15.3 Hz), 7.88 (d, 2H, J=7.5 Hz), 7.76 (t, 1H, J=4.8 Hz), 7.63 (d, 1H, J=15.3 Hz), 7.16 (s, 1H), 6.67 (s, 1H), 3.86 (s, 6H), 3.16 (br s, 4H), 2.76 (quartet, 2H, J=6.9 Hz), 2.15 (m, 10H), 2.06 (s, 3H), 1.80 (br s, 4H), 1.45 (quintet, 2H, J=6.9 Hz). HRMS (ESI) Calcd. for C29H40N4O5S: 557.2798 [(M+H)+]; Found: 557.2798.

Workup

  1. customThe reaction mixture was quenched with water (75 mL)
  2. extractionextracted ethyl acetate (3×50 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to a red solid

Sources & evidence

ORD record
ord-2a168acdbf824628a60d5868cbd61ee7
Source dataset
uspto-grants-2007_02
Patent number
US07173129B2

Reaction notes

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