Sodium Iodide → 4-(3-Chloro-4-fluoro-phenylamino)-7-methoxy-6-pyrrolidin-1-yl-quinoline-3-carbonitrile

HRID 548497Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17][CH3:18])[N:13]=[CH:12][C:11]([C:19]#[N:20])=[C:10]2[NH:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[C:24]([Cl:29])[CH:23]=1.N1CCOCC1.[I-].[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:29][C:24]1[CH:23]=[C:22]([NH:21][C:10]2[C:9]3[C:14](=[CH:15][C:16]([O:17][CH3:18])=[C:7]([N:6]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH:8]=3)[N:13]=[CH:12][C:11]=2[C:19]#[N:20])[CH:27]=[CH:26][C:25]=1[F:28]

Participants

Conditions

Temperature: 750 °C

Procedure

A mixture of 2.5 g of 6-(4-chlorobutylamino)-4-(3-chloro-4-fluorophenyamino)-7-methoxy-3-quinolinecarbonitrile, 7.54 g of morpholine, and 0.17 g of sodium iodide in 30 ml of dimethylformamide was stirred at 750° C. for 7 hrs. The mixture was poured into dilute sodium bicarbonate and solid was collected. This material was dissolved in ethylacetate. The solution was dried over magnesium sulfate. The solvent was removed and the residue was chromatographed on silica gel using ethyl acetate-methanol-triethylamine mixtures. A more polar component (0.54 g) was 4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-6-(4-morpholin-4-yl-butylamino)-quinoline-3-carbonitrile; a less polar component (0.28 g) is the compound of this invention, 4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-6-pyrrolidin-l-yl-quinoline-3-carbonitrile, obtained as a yellow solid: mass spectrum electrospray, m/e): M+H 397.4.

Workup

customwas collected
dissolutionThis material was dissolved in ethylacetate
dry with materialThe solution was dried over magnesium sulfate
customThe solvent was removed
customthe residue was chromatographed on silica gel
customobtained as a yellow solid

Sources & evidence

ORD record: ord-842040b65cd84c428fc1f4003781e0ae
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE042376E1

Reaction notes

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