1,4-Dioxane → 4-(1-(5-Chloro-2-(3-((3-fluorophenoxy)methyl)pyrrolidin-1-yl)nicotinamido)cyclopropyl)benzoic acid

HRID 72556노트

반응식

HRID 72556 반응식
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:24]2[CH2:28][CH2:27][CH:26]([CH2:29][O:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=3)[CH2:25]2)=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:8].O1CCOCC1.O.[OH-].[Li+]>O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:24]2[CH2:28][CH2:27][CH:26]([CH2:29][O:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=3)[CH2:25]2)=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1([C:13]2[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:8]

참가 물질

5

반응물 3

HCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrateHCID 67958339Methyl 4-(1-(5-chloro-2-(3-((3-fluorophenoxy)methyl)pyrrolidin-1-yl)nicotinamido)cyclopropyl)benzoate

생성물 1

HCID 573773554-(1-(5-Chloro-2-(3-((3-fluorophenoxy)methyl)pyrrolidin-1-yl)nicotinamido)cyclopropyl)benzoic acid수율 51%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of methyl 4-(1-(5-chloro-2-(3-((3-fluorophenoxy)methyl)pyrrolidin-1-yl)nicotinamido)cyclopropyl)benzoate (D200) (37 mg, 0.070 mmol) in a mixture 1,4-dioxane and water (3:1) (2 ml) lithium hydroxide monohydrate (10 mg, 0.238 mmol) was added and the mixture was stirred 20 min (4 cycles of 5 min each) under microwaves irradiation. After solvent evaporation the residue was diluted with water (5 ml) and 1M HCl (5 ml) and extracted with ethylacetate (3×10 ml). Collected organics after solvent evaporation afforded a residue that was purified by ISOLUTE Spe-Si (1 g) eluting with a mixture dichloromethane/methanol 98:2. Collected fractions after solvent evaporation afforded the title compound (E76) (18.2 mg)

후처리

  1. customunder microwaves irradiation
  2. customAfter solvent evaporation the residue
  3. additionwas diluted with water (5 ml) and 1M HCl (5 ml)
  4. extractionextracted with ethylacetate (3×10 ml)
  5. customCollected organics after solvent evaporation
  6. customafforded a residue that
  7. customwas purified by ISOLUTE Spe-Si (1 g)
  8. washeluting with a mixture dichloromethane/methanol 98:2
  9. customCollected fractions after solvent evaporation

출처 및 근거

ORD 기록
ord-75ba6ba62431407f8959d271c8005641
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828987B2

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