3-Chloroaniline → HCID 57899105, compound

HRID 76075Notes

Reaction equation

HRID 76075 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl[C:10]1[N:15]=[N:14][C:13]([C:16]2[CH:30]=[CH:29][C:19]([C:20]([NH:22][C:23]([CH3:28])([CH3:27])[C:24]([OH:26])=[O:25])=[O:21])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:10]2[N:15]=[N:14][C:13]([C:16]3[CH:17]=[CH:18][C:19]([C:20]([NH:22][C:23]([CH3:27])([CH3:28])[C:24]([OH:26])=[O:25])=[O:21])=[CH:29][CH:30]=3)=[CH:12][CH:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 79323-ChloroanilineHCID 86634693HCID 86634693, compound

Product 1

HCID 57899105HCID 57899105, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A 1-dram vial was charged with 3-chloroaniline (0.2 Ml, excess) and 2-[4-(6 chloro-pyridazin-3-yl)-benzoylamino]-2-methyl-propionic acid (0.75 g) as a solid. The vial was heated to 100° C. for 1.5 h. The crude reaction mixture was then dissolved in 2 Ml DMF and then purified by reverse-phase preparative HPLC to afford the title compound: 1H NMR (400 MHz, DMSO-D6) δ ppm 1.47 (s, 6H), 7.03 (dd, J=7.45, 1.64 Hz, 1H), 7.28 (d, J=9.35 Hz, 1H), 7.36 (t, J=8.08 Hz, 1H), 7.56 (dd, J=8.34, 1.26 Hz, 1H), 7.99 (d, J=8.59 Hz, 2H), 8.12-8.19 (m, 4H), 8.52 (s, 1H), 9.71 (s, 1H); (M+H)+411.0.

Workup

  1. customThe crude reaction mixture
  2. custompurified by reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-f79ad0811c9c46b79ea361174d36cf3c
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

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