Acetic Acid → HCID 52934273, compound

HRID 1043011Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:18][C@@H:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH3:20])=[C:12]([NH2:17])[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:27][CH3:28])=[C:5]([CH3:29])[O:4][N:3]=1.CC(O)=O.[N:34]([O-])=O.[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl.O>[CH3:1][C:2]1[C:6]([C:7]2[C:8]([O:27][CH3:28])=[CH:9][C:10]3[C:11]4[N:18]([C@@H:19]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[CH3:20])[N:34]=[N:17][C:12]=4[CH:13]=[N:14][C:15]=3[CH:16]=2)=[C:5]([CH3:29])[O:4][N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 7-(3,5-dimethyl-4-isoxazolyl)-6-(methoxy)-N4-[(1R)-1-phenylethyl]-3,4-quinolinediamine (for a preparation see Intermediate 39, 0.2 g, 0.515 mmol) in DCM (10 ml) cooled at 0° C., were added AcOH (0.5 ml) and a solution of sodium nitrite (0.07 g) in water (1 ml). The mixture was stirred at room temperature overnight. The reaction mixture was treated with saturated aqueous Sodium hydrogen carbonate and extracted with DCM. The organic phase was dried over Na2SO4, evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (DCM/MeOH, 95:5). The solid was triturated in diisopropyl ether to give the title compound as a green powder (0.18 g, 87.5%).

Workup

extractionextracted with DCM
dry with materialThe organic phase was dried over Na2SO4
customevaporated under reduced pressure
customThe residue was purified by flash chromatography on silica gel (DCM/MeOH, 95:5)
customThe solid was triturated in diisopropyl ether

Sources & evidence

ORD record: ord-91703c06fa314a17a75c2021840f1522
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557984B2

Reaction notes

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