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2-Fluorobenzoic acid → N-(4-Chloro-5-(1-(4-chlorophenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-2-fluorobenzyl)-2-fluorobenzamide

HRID 59537
Notes
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Reaction equation

HRID 59537 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[NH2:15][CH2:16][C:17]1[C:18]([F:37])=[CH:19][C:20]([Cl:36])=[C:21]([C:23]2[NH:24][C:25](=[O:35])[N:26]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[N:27]=2)[CH:22]=1.CCN(C(C)C)C(C)C>C1COCC1.CN(C=O)C>[Cl:36][C:20]1[C:21]([C:23]2[NH:24][C:25](=[O:35])[N:26]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[N:27]=2)=[CH:22][C:17]([CH2:16][NH:15][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[F:1])=[C:18]([F:37])[CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 99352-Fluorobenzoic acidHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 1366448485-(5-(aminomethyl)-2-chloro-4-fluorophenyl)-2-(4-chlorophenyl)-2H-1,2,4-triazol-3 (4H)-one

Product 1

HCID 136246041N-(4-Chloro-5-(1-(4-chlorophenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-2-fluorobenzyl)-2-fluorobenzamide
Yield 9.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-fluoro benzoic acid (0.400 g), thionyl chloride (20 mL) and DMF (cat. amt.) was refluxed for 5 h and excess of solvent was removed under reduced pressure to obtain crude product. The obtained crude product was added to the solution of 5-(5-(aminomethyl)-2-chloro-4-fluorophenyl)-2-(4-chlorophenyl)-2H-1,2,4-triazol-3 (4H)-one (Intermediate-78, 0.250 g) and DIPEA (1.0 mL) in THF (20 mL) and the reaction mass was stirred for 3 h. After completion of reaction, reaction mass was quenched with water and extracted with ethyl acetate. The organic layer was separated, concentrated to afford 0.032 g of the desired product. 1H NMR (300 MHz, DMSO): δ 4.53 (br s, 2H), 7.29 (m, 2H), 7.70 (m, 3H), 7.78 (m, 3H), 7.95 (br s, 2H), 8.94 (br s, 1H), 12.63 (br s, 1H); MS (m/z): 475.39 (M+H)+.

Workup

  1. temperaturewas refluxed for 5 h and excess of solvent
  2. customwas removed under reduced pressure
  3. customto obtain crude product
  4. customThe obtained crude product
  5. customAfter completion of reaction, reaction mass
  6. customwas quenched with water
  7. extractionextracted with ethyl acetate
  8. customThe organic layer was separated
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-aaa69057702d4e17bd5a5c8ee6c701e5
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09439890B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes