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Acetic Acid → 6-Amino-5-((3-(3-methylfuran-2-carboxamido)phenyl)ethynyl)nicotinic acid

HRID 607432
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HRID 607432 반응식
[NH2:1][C:2]1[C:11]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([C:23]3[O:24][CH:25]=[CH:26][C:27]=3[CH3:28])=[O:22])[CH:15]=2)=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][N:3]=1.[OH-].[Na+].C(O)(=O)C.CCOC(C)=O>C1COCC1>[NH2:1][C:2]1[C:11]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([C:23]3[O:24][CH:25]=[CH:26][C:27]=3[CH3:28])=[O:22])[CH:15]=2)=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1
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참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 57657938Methyl 6-amino-5-((3-(3-methylfuran-2-carboxamido)phenyl)ethynyl)nicotinate

생성물 1

HCID 576578956-Amino-5-((3-(3-methylfuran-2-carboxamido)phenyl)ethynyl)nicotinic acid수율 93.2%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
50 °C

실험 절차

Methyl 6-amino-5-((3-(3-methylfuran-2-carboxamido)phenyl)ethynyl)nicotinate (0.550 g, 1.47 mmol) was dissolved in THF (15 mL) and then treated with 1.0 M NaOH (7.33 mL, 7.33 mmol). The reaction mixture was heated to 50° C. Once the reaction was done by TLC, the reaction was cooled to room temperature and then acidified with acetic acid. The reaction mixture was taken up in of EtOAc (˜15 mL) then extracted with H2O (2×15 mL). The water layer then was re-washed with EtOAc (˜15 mL) and the combined organic layers were dried over anhydrous Na2SO4(s). The mixture was then filtered and concentrated in vacuo to give the title compound (0.495 g, 1.37 mmol).

후처리

  1. temperaturethe reaction was cooled to room temperature
  2. extractionthen extracted with H2O (2×15 mL)
  3. washThe water layer then was re-washed with EtOAc (˜15 mL)
  4. dry with materialthe combined organic layers were dried over anhydrous Na2SO4(s)
  5. filtrationThe mixture was then filtered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c6cc4b2873b748a9a3d004773da8e659
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07915443B2

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