Dimethylamine → 4-(4-Chloro-2-fluoro-5-hydroxy-phenylamino)-7-(3-dimethylamino-propoxy)-6-methoxy-quinoline-3-carbonitrile

HRID 612041Notes

Reaction equation

[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH2:23][CH2:24][CH2:25]Cl)=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:27]#[N:28])=[C:4]([F:29])[CH:3]=1.[I-].[Na+].[CH3:32][NH:33][CH3:34]>O1CCCC1>[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH2:23][CH2:24][CH2:25][N:33]([CH3:34])[CH3:32])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:27]#[N:28])=[C:4]([F:29])[CH:3]=1

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of 0.8 g (1.83 mmol) of 4-(4-chloro-2-fluoro-5-hydroxy-phenylamino)-7-(3-chloro-propoxy)-6-methoxy-quinoline-3-carbonitrile and 0.055 g of sodium iodide in 15.6 ml of 2M dimethylamine in tetrahydrofuran was placed in a sealed tube and heated to 125° C. for 2.5 hr. The solvent was removed and the residue was mixed with warm ethyl acetate and saturated sodium bicarbonate solution. The organic layer was separated and dried over magnesium sulfate. Solvent was removed and the residue was treated with with ethyl acetate-ether depositing a solid and giving 0.51 g of the title compound as a off-white solid: mass spectrum (electrospray, m/e) M+H 445.0; (M+2H)+2 243.4.

Workup

customwas placed in a sealed tube
customThe solvent was removed
additionthe residue was mixed with warm ethyl acetate and saturated sodium bicarbonate solution
customThe organic layer was separated
dry with materialdried over magnesium sulfate
customSolvent was removed
additionthe residue was treated with with ethyl acetate-ether depositing a solid

Sources & evidence

ORD record: ord-05c3ec6d00e240bf98e5c1ab3981b0ff
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06002008

Reaction notes

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