Sodium Iodide → 7-(2-[1,4']Bipiperidinyl-1'-yl-ethoxy)-6-methoxy-4-(4-phenoxy-phenylamino)-quinoline-3-carbonitrile

HRID 269782Notes

Reaction equation

Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:31][CH3:32].[N:33]1([CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.[I-].[Na+]>COCCOC>[N:33]1([CH:39]2[CH2:44][CH2:43][N:42]([CH2:2][CH2:3][O:4][C:5]3[CH:14]=[C:13]4[C:8]([C:9]([NH:17][C:18]5[CH:23]=[CH:22][C:21]([O:24][C:25]6[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=6)=[CH:20][CH:19]=5)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]4)=[CH:7][C:6]=3[O:31][CH3:32])[CH2:41][CH2:40]2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

Conditions

Temperature: 137.5 °C

Procedure

A mixture of 222.5 mg (0.5 mmol) of 7-(2-chloroethoxy)-6-methoxy-4-(4-phenoxyphenylamino)quinoline-3-carbonitrile, 841.4 mg (5.0 mmol) of 4-piperidinopiperidine and 49.5 mg (0.33 mmol) of sodium iodide in 6.0 mL of ethylene glycol dimethyl ether are heated in a sealed tube at 135-140° C. for 17 hours to yield the crude product. Solvents are removed in vacuo. Purification of the oily residue is carried out by preparative thin layer chromatography (eluting with 85:15 dichloromethane/methanol) to provide 137.7 mg of 7-(2-[1,4′]bipiperidinyl-1′-yl-ethoxy)-6-methoxy-4-(4-phenoxy-phenylamino)-quinoline-3-carbonitrile as a light yellow solid, mp 141° C. (decompose).

Workup

customto yield the crude product
customSolvents are removed in vacuo
customPurification of the oily residue
washis carried out by preparative thin layer chromatography (eluting with 85:15 dichloromethane/methanol)

Sources & evidence

ORD record: ord-9d44d3b9d57840fd968efdaa32841f6c
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449460B2

Reaction notes

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