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Pyridine → 2-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropanamide

HRID 218167
Notes
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Reaction equation

HRID 218167 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4([C:23]([CH3:28])([CH3:27])[C:24](O)=[O:25])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[N:29]1C=CC=CC=1.N1C(F)=NC(F)=NC=1F>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4([C:23]([CH3:28])([CH3:27])[C:24]([NH2:29])=[O:25])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 687056802-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropanoic acid

Product 1

HCID 592511432-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropanamide

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

(g) 2-(4-(1-(4-Fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropanoic acid (50 mg, 0.13 mmol) was dissolved in 5 mL DCM, 32 uL pyridine, and treated with 27 uL cyanuric fluoride. After 1 h, the reaction was extracted from NaHCO3 with EtOAc×3. The combined organic layers were dried over MgSO4, filtered, concentrated and taken up in 2 mL NMP and treated with triethylamine (100 uL) and NH4Cl (50 mg). The reaction was purified by HPLC to give 23 mg of 2-(4-(1-(4-fluorophenyl)-1H-indazol-5-yl)tetrahydro-2H-pyran-4-yl)-2-methylpropanamide. (M+H)+=382.

Workup

  1. extractionthe reaction was extracted from NaHCO3 with EtOAc×3
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additiontreated with triethylamine (100 uL) and NH4Cl (50 mg)
  6. customThe reaction was purified by HPLC

Sources & evidence

ORD record
ord-b218f9866f4140d8bd9e8366eeab46bf
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08198311B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes