Water → 3-{2,5-Dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoylamino}-propionic acid

HRID 1967014

반응식

HRID 1967014 반응식
C([O:3][C:4](=[O:40])[CH2:5][CH2:6][NH:7][C:8](=[O:39])[C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([O:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][C:18]=2[C:23]([N:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]([CH:35]3[CH2:37][CH2:36]3)[CH2:27][CH2:26]2)=[O:24])=[CH:11][C:10]=1[Cl:38])C.O.O.[OH-].[Li+]>O1CCOCC1>[Cl:38][C:10]1[CH:11]=[C:12]([O:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][C:18]=2[C:23]([N:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]([CH:35]3[CH2:37][CH2:36]3)[CH2:27][CH2:26]2)=[O:24])[C:13]([Cl:15])=[CH:14][C:9]=1[C:8]([NH:7][CH2:6][CH2:5][C:4]([OH:40])=[O:3])=[O:39]

참가 물질

5

반응물 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 533122803-{2,5-Dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoylamino}-propionic acid ethyl ester

생성물 1

HCID 533122813-{2,5-Dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoylamino}-propionic acid수율 86.3%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of 0.85 g (1.46 mmol) 3-{2,5-dichloro-4-[3-(4-cyclopropyl-3,4-dihydro-2H-quinoxaline-1-carbonyl)-pyridin-4-yloxy]-benzoylamino}-propionic acid ethyl ester (Example 33) in 7.5 mL dioxane were added 7.5 mL water and 0.076 g (1.81 mmol) lithium hydroxide monohydrate. The resulting suspension was stirred for 2.25 hours at room temperature and dioxane was removed by evaporation. The pH of the solution was adjusted to 2.5 by adding 1.9 mL 1M aqueous hydrochloric acid and the suspension was stirred for 2 hours at room temperature. The suspension was filtered, the filter cake washed with water and dried under high vacuum to give 0.70 g (86%) of the desired compound as an off-white solid. MS (ESI): m/z=555.12 [M+H]+.

후처리

  1. customdioxane was removed by evaporation
  2. additionby adding 1.9 mL 1M aqueous hydrochloric acid
  3. stirringthe suspension was stirred for 2 hours at room temperature
  4. filtrationThe suspension was filtered
  5. washthe filter cake washed with water
  6. customdried under high vacuum

출처 및 근거

ORD 기록
ord-5e02d2565cc0495cbb52ed7e2a34636e
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420647B2

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