Triethylamine → HCID 21913002, compound

HRID 1008094Notes

Reaction equation

HRID 1008094 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][N:14]1[C:22]2[C:21]([Br:23])=[CH:20][N:19]=[C:18]([NH2:24])[C:17]=2[N:16]=[C:15]1[CH2:25][CH2:26][CH3:27].[Cl:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1>ClCCl>[NH2:24][C:18]1[C:17]2[N:16]=[C:15]([CH2:25][CH2:26][CH3:27])[N:14]([CH2:13][CH2:12][O:11][CH2:10][CH2:9][NH:8][C:33](=[O:34])[C:32]3[CH:36]=[CH:37][C:29]([Cl:28])=[CH:30][CH:31]=3)[C:22]=2[C:21]([Br:23])=[CH:20][N:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 21912890HCID 21912890, compound

Product 1

HCID 21913002HCID 21913002, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.07 g, 0.66 mmol) was added to a solution of 1-[2-(2-aminoethoxy)ethyl]-7-bromo-2-propyl-1H-imidazo[4,5-c]pyridin-4-amine (0.15 g, 0.44 mmol) in dichloromethane ( 2 mL). 4-Chlorobenzoyl chloride (0.09 g, 0.53 mmol) was added dropwise to the reaction mixture. The reaction mixture was stirred at ambient temperature for 10 minutes at which time analysis by thin layer chromatography indicated that the reaction was complete. The reaction mixture was partitioned between dichloromethane (30 mL) and saturated aqueous sodium bicarbonate (20 mL). The layers were separated. The organic layer was washed sequentially with saturated aqueous ammonium chloride (20 mL) and brine (20 mL), dried over sodium sulfate, filtered and then concentrated under reduced pressure to provide 0.23 g of a clear, glassy solid. The crude material was purified by chromatography (silica gel eluting with 95:5 dichloromethane:methanol) to provide 0.05 g of N-{2-[2-(4-amino-7-bromo-2-propyl-1H-imidazo[4,5-c]pyridin-1-yl)ethoxy]ethyl}-4-chlorobenzamide as a white amorphous solid.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane (30 mL) and saturated aqueous sodium bicarbonate (20 mL)
  2. customThe layers were separated
  3. washThe organic layer was washed sequentially with saturated aqueous ammonium chloride (20 mL) and brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto provide 0.23 g of a clear, glassy solid
  8. customThe crude material was purified by chromatography (silica gel eluting with 95:5 dichloromethane:methanol)

Sources & evidence

ORD record
ord-3cee7f21fc6c46d4aeb0f168e0c1849c
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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