Triethylamine → Methyl 5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]-2-{[(prop-2-en-1-yloxy)-carbamoyl]amino}benzoate

HRID 535451Notes

Reaction equation

HRID 535451 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][CH3:36])[C:27]=2[CH3:37])=[O:25])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].[CH2:38]([O:41][NH2:42])[CH:39]=[CH2:40].C(N(CC)CC)C>O1CCOCC1.O>[CH3:36][O:35][C:28]1[C:27]([CH3:37])=[C:26]([C:24]([C:21]2[CH:22]=[CH:23][C:14]([NH:13][C:5](=[O:11])[NH:42][O:41][CH2:38][CH:39]=[CH2:40])=[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 8471TriethylamineHCID 94429TriphosgeneHCID 420841O-AllylhydroxylamineHCID 66653263Methyl 2-amino-5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]benzoate

Product 1

HCID 86683451Methyl 5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]-2-{[(prop-2-en-1-yloxy)-carbamoyl]amino}benzoateYield 160%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

0.251 g (0.83 mmol) of triphosgene diluted in 3 ml of dioxane is added, under an inert atmosphere at ambient temperature, to 0.4 g (1.18 mmol) of methyl 2-amino-5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]benzoate in 10 ml of dioxane. After stirring for 2.5 hours, 0.267 g (2.36 mmol) of O-prop-2-en-1-ylhydroxylamine and 0.82 ml (5.91 mmol) of triethylamine are added. The reaction medium is stirred for one hour and then hydrolysed with water. The aqueous phase is extracted with dichloromethane. The organic phase obtained is washed with a 1N aqueous solution of hydrochloric acid and a saturated aqueous solution of sodium chloride, and then dried over sodium sulphate, filtered, and concentrated under reduced pressure. 0.581 g of a yellow solid is obtained.

Workup

  1. stirringThe reaction medium is stirred for one hour
  2. extractionThe aqueous phase is extracted with dichloromethane
  3. customThe organic phase obtained
  4. washis washed with a 1N aqueous solution of hydrochloric acid
  5. dry with materiala saturated aqueous solution of sodium chloride, and then dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5fbf785230f34dc8baeb183daea3150e
Source dataset
uspto-grants-2014_10
Patent number
US08859544B2

Reaction notes

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