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Hydrochloric Acid → 4-(1-(5-Chloro-2-(3-(3-(piperazin-1-yl)phenoxy)azetidin-1-yl)nicotinamido)cyclopropyl)benzoic acid

HRID 72546
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HRID 72546 반응식
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:24]2[CH2:27][CH:26]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([N:35]4[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]4)[CH:30]=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].[OH-].[Na+].Cl>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:24]2[CH2:27][CH:26]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([N:35]4[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]4)[CH:30]=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]
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참가 물질

5

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HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67958605Methyl 4-(1-(5-chloro-2-(3-(3-(piperazin-1-yl)phenoxy)azetidin-1-yl)nicotinamido)cyclopropyl)benzoate

생성물 1

HCID 573782224-(1-(5-Chloro-2-(3-(3-(piperazin-1-yl)phenoxy)azetidin-1-yl)nicotinamido)cyclopropyl)benzoic acid수율 77.5%

시약·촉매·용매 1

HCID 21886435
1,4-Dioxane--water (1/1)
용매

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온도
60 °C

실험 절차

To a solution of methyl 4-(1-(5-chloro-2-(3-(3-(piperazin-1-yl)phenoxy)azetidin-1-yl)nicotinamido)cyclopropyl)benzoate (D156) (105 mg, 0.186 mmol) in a mixture 1-4-dioxane/water (3 ml/1 ml), 1N NaOH (0.28 ml) was added. The reaction mixture was heated to 60° C. overnight. After cooling at room temperature, the reaction mixture was acidified with 1N HCl (pH=1) and the solvents were evaporated in vacuo. The residue was loaded on Porapak RXN RP cartridge (5 g) eluting with water+0.1% acetic acid/acetonitrile+0.1% acetic acid from 90/10 to 0/100. Collected fractions after solvente evaporation afforded the title compound (E21) (79 mg).

후처리

  1. temperatureAfter cooling at room temperature
  2. customthe solvents were evaporated in vacuo
  3. washeluting with water+0.1% acetic acid/acetonitrile+0.1% acetic acid from 90/10 to 0/100
  4. customCollected fractions after solvente evaporation

출처 및 근거

ORD 기록
ord-7ba99a574dfc46209a8df88afc833fc3
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08828987B2

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