2-Fluoro-4-iodobenzoyl isocyanate → Tert-butyl 2-(2-chloro-5-(cyclopropanecarboxamidomethyl)phenyl)-2-((2-fluoro-4-iodobenzoyl)carbamoyl)hydrazinecarboxylate

HRID 59330Notes

Reaction equation

HRID 59330 reaction equation
[F:1][C:2]1[CH:12]=[C:11]([I:13])[CH:10]=[CH:9][C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH:22][C:23]([CH:25]2[CH2:27][CH2:26]2)=[O:24])=[CH:17][C:16]=1[NH:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]>C(Cl)Cl>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH:22][C:23]([CH:25]2[CH2:27][CH2:26]2)=[O:24])=[CH:17][C:16]=1[N:28]([C:7](=[O:8])[NH:6][C:4](=[O:5])[C:3]1[CH:9]=[CH:10][C:11]([I:13])=[CH:12][C:2]=1[F:1])[NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]

Participants

4

Reactant 2

HCID 900186562-Fluoro-4-iodobenzoyl isocyanateHCID 90019289Tert-butyl 2-(2-chloro-5-(cyclopropanecarboxamidomethyl) phenyl)hydrazinecarboxylate

Product 1

HCID 90065811Tert-butyl 2-(2-chloro-5-(cyclopropanecarboxamidomethyl)phenyl)-2-((2-fluoro-4-iodobenzoyl)carbamoyl)hydrazinecarboxylateYield 18.5%

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-fluoro-4-iodobenzoyl isocyanate (Intermediate-47, 0.500 g, 1.71 mmol), tert-butyl 2-(2-chloro-5-(cyclopropanecarboxamidomethyl)phenyl)hydrazine carboxylate (0.582 g, 1.71 mmol) and DCM (20 mL) to afford 0.200 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 0.69 (m, 4H), 1.42 (s, 9H), 1.56 (m, 1H), 4.17 (d, J=5.7 Hz, 2H), 6.58-6.63 (m, 2H), 7.18 (d, J=8.1 Hz, 1H), 7.30 (m, 3H), 7.63-7.79 (m, 2H), 8.53 (m, 1H), 8.90 (s, 1H); MS (m/z): 630.85 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-80464b0debb147e6b4296afc3d80717b
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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