Trifluoroacetic acid → N-(4-chloro-3-(3-(3-fluoro-4-iodophenyl)-4,5-dihydro-5-oxo-1,2,4-triazol-1-yl)benzyl)isobutyramide

HRID 59554Notes

Reaction equation

HRID 59554 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[I:13])[C:5]([N:7]=[C:8]=[O:9])=O.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH:22][C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])=[CH:17][C:16]=1[NH:28][NH:29]C(OC(C)(C)C)=O.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH:22][C:23](=[O:27])[CH:24]([CH3:26])[CH3:25])=[CH:17][C:16]=1[N:28]1[C:8](=[O:9])[NH:7][C:5]([C:4]2[CH:10]=[CH:11][C:12]([I:13])=[C:2]([F:1])[CH:3]=2)=[N:29]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 900191213-Fluoro-4-iodobenzoyl isocyanateHCID 90065680tert-Butyl 2-(2-chloro-5-{[(2-methylpropanoyl)amino]methyl}phenyl)hydrazinecarboxylate

Product 1

HCID 136492380N-(4-chloro-3-(3-(3-fluoro-4-iodophenyl)-4,5-dihydro-5-oxo-1,2,4-triazol-1-yl)benzyl)isobutyramideYield 74.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example-83 by using 3-fluoro-4-iodobenzoyl isocyanate (Intermediate-102, 1.0 g), tert-butyl 2-(2-chloro-5-{[(2-methylpropanoyl)amino]methyl}phenyl)hydrazinecarboxylate (Intermediate-97, 0.800 g), DCM (15 mL), and trifluoro acetic acid (3.0 mL) to afford 0.900 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 1.30 (s, 6H), 2.43-2.45 (m, 1H), 4.26 (m, 2H), 7.01 (m, 1H), 7.46-7.49 (m, 1H), 7.63-7.66 (m, 1H), 7.84-7.91 (m, 1H), 8.01-8.06 (m, 1H), 8.22 (s, 1H), 8.36 (br s, 1H), 12.66 (m, 1H); MS (m/z): 515.21 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-4408a01aadfb4207ae28551ec48ee463
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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