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

HRID 535442

반응식

HRID 535442 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7fe39e2e149f470199cb02595e447c39
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859544B2

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