Trifluoroacetic acid → HCID 136612545, compound

HRID 59412Notes

Reaction equation

HRID 59412 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.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][NH:29]C(OC(C)(C)C)=O)=[CH:24][C:23]=1[CH3:37].FC(F)(F)C(O)=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:28]([C:25]2[CH:26]=[CH:27][C:22]([Cl:21])=[C:23]([CH3:37])[CH:24]=2)[N:29]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 900192862-Chloro-5-((2,2,2-trifluoroacetamido)methyl)benzoyl isocyanateHCID 90065740HCID 90065740, compound

Product 1

HCID 136612545HCID 136612545, compoundYield 44,921.301%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in Example-83 by using 2-chloro-5-((2,2,2-trifluoroacetamido)methyl)benzoyl isocyanate (step-3 of Intermediate-26, 1.0 g, 0.003 mmol), tert-butyl 2-(4-chloro-3-methylphenyl)hydrazinecarboxylate (Intermediate-105, 1.500 g), DCM (20 mL), and trifluoro acetic acid (5.0 mL) to afford 0.600 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 2.38 (s, 3H), 4.45 (d, J=5.4 Hz, 2H), 7.53 (d, J=9.3 Hz, 2H), 7.67 (s, 2H), 7.82 (d, J=8.1 Hz, 1H), 7.92 (s, 1H), 10.08 (t, 1H), 12.61 (s, 1H); MS (m/z): 445.31 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-2a96074be6c5494e958eb34f4f96892d
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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