Tert-butyl 2-(3-methoxy-4-nitrophenyl)hydrazinecarboxylate → Tert-butyl 2-((2-chloro-5-((2,2,2-trifluoroacetamido) methyl)benzoyl)carbamoyl)-2-(3-methoxy-4-nitrophenyl)hydrazinecarboxylate

HRID 508782Notes

Reaction equation

HRID 508782 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:5].[CH3:21][O:22][C:23]1[CH:24]=[C:25]([NH:32][NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH:26]=[CH:27][C:28]=1[N+:29]([O-:31])=[O:30]>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:18])([F:19])[F:17])=[CH:9][C:3]=1[C:4]([NH:6][C:7]([N:32]([C:25]1[CH:26]=[CH:27][C:28]([N+:29]([O-:31])=[O:30])=[C:23]([O:22][CH3:21])[CH:24]=1)[NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 90018942Tert-butyl 2-(3-methoxy-4-nitrophenyl)hydrazinecarboxylateHCID 900192862-Chloro-5-((2,2,2-trifluoroacetamido)methyl)benzoyl isocyanate

Product 1

HCID 90019688Tert-butyl 2-((2-chloro-5-((2,2,2-trifluoroacetamido) methyl)benzoyl)carbamoyl)-2-(3-methoxy-4-nitrophenyl)hydrazinecarboxylateYield 74.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure described in step-1 of Intermediate-9 by using 2-chloro-5-((2,2,2-trifluoroacetamido)methyl)benzoyl isocyanate (step-3 of Intermediate-26, 1.400 g, 4.57 mmol), tert-butyl 2-(3-methoxy-4-nitrophenyl)hydrazinecarboxylate (step-3 of Intermediate-32, 1.30 g, 4.57 mmol) and DCM 30 mL) to afford 2.0 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 1.33-1.46 (m, 9H), 3.87 (s, 3H), 4.40 (s, 2H), 7.06 (d, J=8.4 Hz, 1H), 7.32-7.36 (m, 3H), 7.45-7.52 (m, 1H), 7.96 (d, J=8.7 Hz, 1H), 9.92 (s, 1H), 10.07 (br s, 1H), 11.13 (br s, 1H); MS (m/z): 589.69 (M)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-08ea229229ed437b9c235b631372499c
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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