Triethylamine → HCID 12109134, compound

HRID 2084639Notes

Reaction equation

HRID 2084639 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:23][CH2:24][CH2:25][CH2:26][NH2:27])[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:8]=2[N:22]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[CH3:35][N:36]([CH3:56])[CH2:37][CH2:38][O:39][CH:40]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:41]1[CH:49]=[CH:48][C:44]([C:45](Cl)=[O:46])=[CH:43][CH:42]=1>ClCCl>[CH2:1]([C:5]1[N:6]([CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:45](=[O:46])[C:44]2[CH:43]=[CH:42][C:41]([CH:40]([O:39][CH2:38][CH2:37][N:36]([CH3:35])[CH3:56])[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[CH:49][CH:48]=2)[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([O:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:8]=2[N:22]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 121091334-[[2-(Dimethylamino)ethoxy](phenyl)methyl]benzoyl chlorideHCID 121091434-(2-butyl-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butan-1-amine

Product 1

HCID 12109134HCID 12109134, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under a nitrogen atmosphere, 4-(2-butyl-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butan-1-amine (122 mg, 0.33 mmol) was dissolved in dichloromethane and triethylamine (0.093 mL, 0.67 mmol). The solution was cooled in an ice-water bath and 4-[[2-(dimethylamino)ethoxy](phenyl)methyl]benzoyl chloride (106 mg, 0.33 mmol) was dissolved/slurried in dichloromethane and added dropwise. The ice bath was removed and the reaction was stirred for an additional 16 hours. The reaction was quenched with 10% aqueous sodium carbonate. The phases were separated and the aqueous fraction was extracted with dichloromethane. The organic fractions were combined, washed with water followed by brine, dried (Na2SO4), decanted and evaporated to yield a yellow oil. Purification by flash column chromatography (silica gel, 92:8 dichloromethane/methanol gradient to 95:5 dichloromethane/methanol) provided 101 mg of N-[4-(2-butyl-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butyl]-4-[[2-(dimethylamino)ethoxy](phenyl)methyl]benzamide as a pale yellow solid. The product was determined to be 97+% pure by HPLC.

Workup

  1. temperatureThe solution was cooled in an ice-water bath
  2. additionadded dropwise
  3. customThe ice bath was removed
  4. customThe reaction was quenched with 10% aqueous sodium carbonate
  5. customThe phases were separated
  6. extractionthe aqueous fraction was extracted with dichloromethane
  7. washwashed with water
  8. dry with materialdried (Na2SO4)
  9. customdecanted
  10. customevaporated
  11. customto yield a yellow oil
  12. customPurification by flash column chromatography (silica gel, 92:8 dichloromethane/methanol gradient to 95:5 dichloromethane/methanol)

Sources & evidence

ORD record
ord-86c7c60a61e44dc2b776a0e57f9ab595
Source dataset
uspto-grants-2004_04
Patent number
US06716988B2

Reaction notes

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