4-Ethoxyaniline → N-(4-ethoxyphenyl)-8-(2-ethyl-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamide

HRID 427475Notes

Reaction equation

HRID 427475 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:19][CH3:20])=[CH:8][C:7]([C:21](O)=[O:22])=[CH:6][N:5]2[C:24]=1[CH3:25].[B-](F)(F)(F)F.CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.[CH2:48]([O:50][C:51]1[CH:57]=[CH:56][C:54]([NH2:55])=[CH:53][CH:52]=1)[CH3:49]>C(Cl)Cl>[CH2:48]([O:50][C:51]1[CH:57]=[CH:56][C:54]([NH:55][C:21]([C:7]2[CH:8]=[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:19][CH3:20])[C:4]3[N:5]([C:24]([CH3:25])=[C:2]([CH3:1])[N:3]=3)[CH:6]=2)=[O:22])=[CH:53][CH:52]=1)[CH3:49]

Participants

5

Reactant 3

HCID 90764-EthoxyanilineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118239362,3-Dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylic acid

Product 1

HCID 9890296N-(4-ethoxyphenyl)-8-(2-ethyl-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine-6-carboxamideYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3-Dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylic acid (0.15 g, 0.44 mmol) and o-Benzotriazol-1-yl-N,N,N′,N′-Tetramethyluronium tetrafluoroborate (TBTU)(0.14 g, 0.44 mmol) were added to methylene chloride (10 ml). 4-ethoxyanilin(0.19 g, 1.4 mmol) was added and the reaction mixture was stirred at ambient temperature for 72 h. The solvent was evaporated under reduced pressure and the residue was added to a column with silica gel and was purified by chromatography using methylene chloride:methanol (95:5) as eluent. The residue was treated with a hot mixture of hexane:ethyl acetate (2:1) and the product was filtered off and dried to obtain 0.14 g (74%) of the desired compound as white crystals.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was added to a column with silica gel
  3. customwas purified by chromatography
  4. additionThe residue was treated with a hot mixture of hexane:ethyl acetate (2:1)
  5. filtrationthe product was filtered off
  6. customdried

Sources & evidence

ORD record
ord-a123a0544214479c886360d44421ef5a
Source dataset
uspto-grants-2001_11
Patent number
US06313136B1

Reaction notes

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