Propylamine → HCID 66653216, compound

HRID 535460Notes

Reaction equation

HRID 535460 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:23]=[CH:22][C:21]([C:24]([C:26]2[N:34]3[C:29]([CH:30]=[CH:31][CH:32]=[CH:33]3)=[C:28]([O:35][CH2:36][CH2:37][O:38][CH3:39])[C:27]=2[CH3:40])=[O:25])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].C(N(CC)CC)C.[CH2:48]([NH2:51])[CH2:49][CH3:50]>O1CCOCC1.O>[CH3:39][O:38][CH2:37][CH2:36][O:35][C:28]1[C:27]([CH3:40])=[C:26]([C:24]([C:21]2[CH:22]=[CH:23][C:14]([NH:13][C:5](=[O:11])[NH:51][CH2:48][CH2:49][CH3:50])=[C:15]([CH:20]=2)[C:16]([O:18][CH3:19])=[O:17])=[O:25])[N:34]2[C:29]=1[CH:30]=[CH:31][CH:32]=[CH:33]2

Participants

7

Reactant 4

HCID 7852PropylamineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 66653176HCID 66653176, compound

Product 1

HCID 66653216HCID 66653216, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

0.108 g (0.37 mmol) of triphosgene diluted in 1 ml of dioxane is added, under an inert atmosphere at ambient temperature, to 0.2 g (0.52 mmol) of methyl 2-amino-5-{[1-(2-methoxyethoxy)-2-methylindolizin-3-yl]carbonyl}benzoate in 5 ml of dioxane. The reaction medium is stirred for 1 hour at ambient temperature and then 0.22 ml (1.57 mmol) of triethylamine and 0.09 ml (1.05 mmol) of n-propylamine are added. After stirring for 18 hours, the reaction medium is hydrolysed with water. The aqueous phase is extracted with dichloromethane. The organic phase obtained is dried over sodium sulphate, filtered, and concentrated under reduced pressure. The solid obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (95/5) mixture. 170 mg of a yellow solid are obtained.

Workup

  1. stirringAfter stirring for 18 hours
  2. extractionThe aqueous phase is extracted with dichloromethane
  3. customThe organic phase obtained
  4. dry with materialis dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe solid obtained
  8. customis purified by silica gel column chromatography, elution

Sources & evidence

ORD record
ord-ec4f253fddc846fb8f77bcf2833ef244
Source dataset
uspto-grants-2014_10
Patent number
US08859544B2

Reaction notes

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