2-Chloro-5-((2,2,2-trifluoroacetamido)methyl)benzoyl isocyanate → methyl 4-(3-(2-chloro-5-((2,2,2-trifluoroacetamido) methyl)phenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)benzoate

HRID 508797Notes

Reaction equation

HRID 508797 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:10]([CH2:13][NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])=[CH:9][C:3]=1[C:4]([N:6]=[C:7]=[O:8])=O.[CH3:21][O:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([NH:31][NH:32]C(OC(C)(C)C)=O)=[CH:27][CH:26]=1)=[O:24]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:12]=[CH:11][C:10]([CH2:13][NH:14][C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])=[CH:9][C:3]=1[C:4]1[NH:6][C:7](=[O:8])[N:31]([C:28]2[CH:27]=[CH:26][C:25]([C:23]([O:22][CH3:21])=[O:24])=[CH:30][CH:29]=2)[N:32]=1

Participants

5

Reactant 2

HCID 900192862-Chloro-5-((2,2,2-trifluoroacetamido)methyl)benzoyl isocyanateHCID 90065642tert-Butyl 2-(4-(methoxycarbonyl)phenyl) hydrazinecarboxylate

Product 1

HCID 136492564methyl 4-(3-(2-chloro-5-((2,2,2-trifluoroacetamido) methyl)phenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)benzoateYield 75.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The title compound was prepared according to the procedure described in step-1 and step-2 of Intermediate-9 by using 2-chloro-5-((2,2,2-trifluoroacetamido)methyl)benzoyl isocyanate (step-3 of Intermediate-26, 1.300 g, 4.2 mmol) and tert-butyl 2-[4-(methoxycarbonyl)phenyl]hydrazinecarboxylate (Intermediate-7, 1.150 g, 3.8 mmol) in TFA (5-7 mL) and DCM (40 mL). The reaction mass was quenched with water and extracted with DCM. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 1.300 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 3.84 (s, 3H), 4.44 (d, J=5.7 Hz, 2H), 7.49 (t, 1H), 7.66 (d, J=8.7 Hz, 2H), 8.04-8.13 (m, 4H), 10.07 (m, 1H), 12.69 (s, 1H); MS (m/z): 453.14 (M−H)−.

Workup

  1. customThe title compound was prepared
  2. customThe reaction mass was quenched with water
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4532df89009146ff8fb33ff84157f72d
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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