(3,4-Dimethoxyphenyl)acetic acid → HCID 16075323, compound

HRID 1795120Notes

Reaction equation

HRID 1795120 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N:15](=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]([CH3:38])[S:25]([C:28]1[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=1)(=[O:27])=[O:26])[NH2:16].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([NH:16]/[N:15]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:24]([CH3:38])[S:25]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:35])([F:36])[F:37])=[CH:30][CH:29]=2)(=[O:27])=[O:26])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 7139(3,4-Dimethoxyphenyl)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69595470HCID 69595470, compound

Product 1

HCID 16075323HCID 16075323, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 31374DimethylacetamideSolvent

Procedure

A flask is charged with (3,4-dimethoxyphenyl)acetic acid (0.34 mmol), 4-dimethylaminopyridine (0.66 mmol), a solution of N-{2-[hydrazonomethyl]phenyl}-N-methyl-4-(trifluoromethyl)benzenesulfonamide (0.33 mmol) in N,N-dimethylacetamide (1 mL), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.33 mmol). The reaction is stirred at room temperature for 18 hours. The reaction is worked up by evaporating the reaction mixture. The product is purified on silica gel with ethyl acetate-methylene chloride mixtures or methanol-methylene chloride mixtures. A 58% yield of N-[2-((E)-{[(3,4dimethoxyphenyl)acetyl]hydrazono}methyl)phenyl]-N-methyl-4-(trifluoromethyl)benzenesulfonamide is obtained. 1H NMR (400 MHz, CDCl3) (mixture of geometric isomers) d 3.25 (s); 3.90 (2s); 4.10 (m); 6.58 (m); 6.87 (m); 6.96 (m); 7.45 (m); 7.82 (m); 8.20 (m); 8.29 (m); 8.90&8.96 (2bs). ESI− for C25H24F3N3O5S: m/z=534 (M−H)−.

Workup

  1. customby evaporating the reaction mixture
  2. customThe product is purified on silica gel with ethyl acetate-methylene chloride mixtures or methanol-methylene chloride mixtures

Sources & evidence

ORD record
ord-763fb70117da4449bb33a565f9dff168
Source dataset
uspto-grants-2006_04
Patent number
US07026339B2

Reaction notes

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