1,1-Dimethoxyethyl(dimethyl)amine → 5-(3-Dimethylamino-acryloyl)-4'-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

HRID 506632Notes

Reaction equation

HRID 506632 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[CH:12]=[C:13]([C:15](=[O:17])[CH3:16])[CH:14]=1)=[O:8])[CH3:5].CO[C:27](OC)([N:29]([CH3:31])[CH3:30])C>>[CH3:1][O:2][CH2:3][CH:4]([NH:6][C:7]([C:9]1[CH:10]=[C:11]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[CH:12]=[C:13]([C:15](=[O:17])[CH:16]=[CH:27][N:29]([CH3:31])[CH3:30])[CH:14]=1)=[O:8])[CH3:5]

Participants

3

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 594325345-Acetyl-4'-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

Product 1

HCID 666781975-(3-Dimethylamino-acryloyl)-4'-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide

Procedure

A solution of 5-acetyl-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide (648 mg, 2 mmol) in N,N-dimethylacetamide dimethyl acetal (0.8 mL) was heated to reflux for 18 hours. The reaction mixture was cooled and volatiles were removed in vacuo. The resulting 188 mg of crude 5-(3-dimethylamino-acryloyl)-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide was used directly in the next step without further purification.

Workup

  1. temperatureto reflux for 18 hours
  2. temperatureThe reaction mixture was cooled
  3. customvolatiles were removed in vacuo
  4. customThe resulting 188 mg of crude 5-(3-dimethylamino-acryloyl)-4′-methyl-biphenyl-3-carboxylic acid (2-methoxy-1-methyl-ethyl)-amide was used directly in the next step without further purification

Sources & evidence

ORD record
ord-8d00351ac3034c89801607d3e4104d44
Source dataset
uspto-grants-2010_08
Patent number
US07786110B2

Reaction notes

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