Dimethylamine → 8-(2-ethyl-6-methylbenzylamino)-N,N,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamide

HRID 427486Notes

Reaction equation

HRID 427486 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]([OH:23])=O)=[CH:6][N:5]2[C:24]=1[CH3:25].[B-](F)(F)(F)F.[CH3:31][N:32](C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)[CH3:33].CNC>C(Cl)Cl>[CH2:19]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[C:12]=1[CH2:11][NH:10][C:9]1[C:4]2[N:5]([C:24]([CH3:25])=[C:2]([CH3:1])[N:3]=2)[CH:6]=[C:7]([C:21]([N:32]([CH3:33])[CH3:31])=[O:23])[CH:8]=1)[CH3:20]

Participants

5

Reactant 3

HCID 674Dimethylamine2×HCID 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 98638838-(2-ethyl-6-methylbenzylamino)-N,N,2,3-tetramethylimidazo[1,2-a]pyridine-6-carboxamideYield 62.4%

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). Dimethylamin (0.063 g, 1.4 mmol) was added and the reaction mixture was stirred at ambient temperature for 4 h. An additional amount of dimethylamin (0.1 ml) was added and the mixture was stirred at room temperature for 20 h. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography using methylene chloride:methanol (9:1) as eluent. The oily product was treated with heptane and the solid that formed was filtered off to give 0.1 g (62%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 20 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by column chromatography
  4. additionThe oily product was treated with heptane
  5. customthe solid that formed
  6. filtrationwas filtered off

Sources & evidence

ORD record
ord-63db1f7cb9ae46cea00d269dcfc37205
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

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