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

HRID 1888919Notes

Reaction equation

HRID 1888919 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-965bdf61f6a84ad093d92e4a1f238577
Source dataset
uspto-grants-2013_08
Patent number
US08501933B2

Reaction notes

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