Tert-butyl 2-(3-methoxy-4-(methoxycarbonyl)phenyl)hydrazinecarboxylate → HCID 90019382, compound

HRID 508794Notes

Reaction equation

HRID 508794 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:6]=[CH:7][C:8]=1[C:9]([O:11][CH3:12])=[O:10].[Cl:22][C:23]1[CH:33]=[CH:32][C:31]([S:34](=[O:40])(=[O:39])[NH:35][CH:36]2[CH2:38][CH2:37]2)=[CH:30][C:24]=1[C:25]([N:27]=[C:28]=[O:29])=[O:26]>C(Cl)Cl>[Cl:22][C:23]1[CH:33]=[CH:32][C:31]([S:34](=[O:40])(=[O:39])[NH:35][CH:36]2[CH2:38][CH2:37]2)=[CH:30][C:24]=1[C:25]([NH:27][C:28]([N:13]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:29])=[O:26]

Participants

4

Reactant 2

HCID 69045843Tert-butyl 2-(3-methoxy-4-(methoxycarbonyl)phenyl)hydrazinecarboxylate2×HCID 900195252-chloro-5-(N-cyclopropylsulfamoyl)benzoyl isocyanate

Product 1

HCID 90019382HCID 90019382, compoundYield 16.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(3-methoxy-4-(methoxycarbonyl)phenyl)hydrazinecarboxylate (Intermediate 14, 1.5 g, 5.08 mmol) in DCM (20 mL) was added 2-chloro-5-(N-cyclopropylsulfamoyl)benzoyl isocyanate (1.6 g, 5.32 mmol). The reaction mass was stirred at RT for 2 h. Excess of solvent was removed under vacuum to afford 0.500 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 0.50 (m, 4H), 1.41 (s, 9H), 2.11 (m, 1H), 3.68-3.75 (m, 6H), 7.59 (d, J=8.7 Hz, 1H), 7.78-7.87 (m, 4H), 8.10 (m, 2H), 8.27 (s, 1H), 8.95 (s, 1H).

Workup

  1. customExcess of solvent was removed under vacuum

Sources & evidence

ORD record
ord-e849212cc27742b79678f676568327e1
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

Loading…