N-methyl-2-pyrrolidone → 7-(4-Pyrrolidin-1-ylpiperidin-1-yl)quinoline-3-carbonitrile

HRID 499115Notes

Reaction equation

HRID 499115 reaction equation
ClC1C=C(N[C:16]2[C:25]3[C:20](=[CH:21][C:22](F)=[CH:23][CH:24]=3)[N:19]=[CH:18][C:17]=2[C:27]#[N:28])C=CC=1SC1N(C)C=CN=1.[CH3:29][N:30]1[CH2:34][CH2:33][CH2:32][C:31]1=O>>[N:30]1([CH:29]2[CH2:21][CH2:20][N:19]([C:22]3[CH:21]=[C:20]4[C:25]([CH:16]=[C:17]([C:27]#[N:28])[CH:18]=[N:19]4)=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 684601654-({3-chloro-4-[(1-methyl-1H-imidazole-2-yl)thio]phenyl)amino)-7-fluoroquinoline-3-carbonitrile

Product 1

HCID 1317282617-(4-Pyrrolidin-1-ylpiperidin-1-yl)quinoline-3-carbonitrile

Conditions

Temperature
105 °C

Procedure

Following the procedure of Example 11, a mixture of 150 mg (0.37 mmol) of 4-({3-chloro-4-[(1-methyl-1H-imidazole-2-yl)thio]phenyl}amino)-7-fluoroquinoline-3-carbonitrile and 339 mg (2.20 mmol) of 4-(1-pyrrolidinylpiperidine) in 1 mL of 1-methyl 2-pyrrolidinone is heated at 105° C. for 17 hours to yield the crude product. Purification by silica gel chromatography (gradient 98:2 methylene chloride/methanol to 9:1 methylene chloride/methanol) gives 66 mg of 4-{3-chloro-4-[(1-methyl-1H-imidazole-2-yl)thio]phenyl}amino)-7-(4-pyrrolidin-1-ylpiperidin-1-yl)quinoline-3-carbonitrile as a yellow solid, mp 125-130° C.

Workup

  1. customto yield the crude product
  2. customPurification by silica gel chromatography (gradient 98:2 methylene chloride/methanol to 9:1 methylene chloride/methanol)

Sources & evidence

ORD record
ord-4926c8b2608e45e79a424e6750af350f
Source dataset
uspto-grants-2010_08
Patent number
US07767671B2

Reaction notes

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