HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 607432
Notes
Print preview

Reaction equation

HRID 607432 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c6cc4b2873b748a9a3d004773da8e659
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07915443B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes