Acetyl chloride → N-[4-({3-chloro-4-[(1-methyl-1H-imidazole-2-yl)thio]phenyl}amino)-3-cyano-7-(4-pyrrolidin-1-ylpiperidin-1-yl)quinolin-6-yl]acetamide

HRID 269779Notes

Reaction equation

HRID 269779 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([N:27]4[CH2:32][CH2:31][CH:30]([N:33]5[CH2:37][CH2:36][CH2:35][CH2:34]5)[CH2:29][CH2:28]4)=[C:23]([NH2:26])[CH:24]=3)[N:19]=[CH:18][C:17]=2[C:38]#[N:39])[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1.C(N(CC)C1C=CC=CC=1)C.[C:51](Cl)(=[O:53])[CH3:52]>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([N:27]4[CH2:28][CH2:29][CH:30]([N:33]5[CH2:37][CH2:36][CH2:35][CH2:34]5)[CH2:31][CH2:32]4)=[C:23]([NH:26][C:51](=[O:53])[CH3:52])[CH:24]=3)[N:19]=[CH:18][C:17]=2[C:38]#[N:39])[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 7061N,N-DiethylanilineHCID 68460429HCID 68460429, compound

Product 1

HCID 68458845N-[4-({3-chloro-4-[(1-methyl-1H-imidazole-2-yl)thio]phenyl}amino)-3-cyano-7-(4-pyrrolidin-1-ylpiperidin-1-yl)quinolin-6-yl]acetamideYield 87.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

By the procedure of Example 27, 0.1 g (0.18 mmol) of 4-({3-chloro-4-[(1-methyl-1H-imidazole-2-yl)thio]phenyl}amino)-6-amino-7-(4-pyrrolidin-1-ylpiperidin-1-yl)quinoline-3-carbonitrile is reacted with 0.3 ml (1.9 mmol) of N,N-diethyl aniline and 0.04 ml (0.56 mmol) of acetyl chloride in 1.5 mL of NMP. The crude residue is purified by silica gel chromatography (gradient 95:5 methylene chloride/methanol to 4:1 methylene chloride/methanol) to give 95 mg of N-[4-({3-chloro-4-[(1-methyl-1H-imidazole-2-yl)thio]phenyl}amino)-3-cyano-7-(4-pyrrolidin-1-ylpiperidin-1-yl)quinolin-6-yl]acetamide as a beige solid, mp 243-255° C.

Workup

  1. customThe crude residue is purified by silica gel chromatography (gradient 95:5 methylene chloride/methanol to 4:1 methylene chloride/methanol)

Sources & evidence

ORD record
ord-47e9a343f939448e90779e6ef4dafe1d
Source dataset
uspto-grants-2008_11
Patent number
US07449460B2

Reaction notes

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