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

HRID 535442

Reaction equation

HRID 535442 reaction equation
Cl[C:2](Cl)([O:4]C(=O)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].C(O)(=O)C.[CH3:42][N:43]([CH3:48])[C:44](=[O:47])[CH2:45][NH2:46].C(N(CC)CC)C>O1CCOCC1.O>[CH3:42][N:43]([CH3:48])[C:44](=[O:47])[CH2:45][NH:46][C:2]([NH: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])=[O:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 533990092-Amino-N,N-dimethylacetamide acetateHCID 66653263Methyl 2-amino-5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]benzoate

Product 1

HCID 66652958Methyl 2-({[2-(dimethylamino)-2-oxoethyl]carbamoyl}amino)-5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]benzoateYield 143.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

0.798 g (2.69 mmol) of triphosgene diluted in 10 ml of dioxane is added, under an inert atmosphere at ambient temperature, to 1.3 g (3.84 mmol) of methyl 2-amino-5-[(1-methoxy-2-methylindolizin-3-yl)carbonyl]benzoate in 50 ml of dioxane. After stirring for 1 hour, 1.25 g (7.68 mmol) of N,N-dimethylglycinamide acetate and 2.68 ml (19.21 mmol) of triethylamine are added. The reaction medium is stirred overnight at ambient temperature and then hydrolysed with water. The aqueous phase is extracted with dichloromethane. The organic phase obtained is dried over sodium sulphate, filtered, and then concentrated under reduced pressure. 1.8 g of a yellow solid are obtained.

Workup

  1. stirringThe reaction medium is stirred overnight at ambient temperature
  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

Sources & evidence

ORD record
ord-7fe39e2e149f470199cb02595e447c39
Source dataset
uspto-grants-2014_10
Patent number
US08859544B2

Linked notes

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