N-methyl-2-pyrrolidone → HCID 86628426, compound

HRID 499116Notes

Reaction equation

HRID 499116 reaction equation
ClC1C=C(N[C:16]2[C:25]3[C:20](=[CH:21][C:22](F)=[C:23](OCCOC)[CH:24]=3)[N:19]=[CH:18][C:17]=2[C:32]#[N:33])C=CC=1SC1N(C)C=CN=1.[CH3:34][N:35]1[CH2:39][CH2:38][CH2:37][C:36]1=O>>[N:35]1([CH:34]2[CH2:21][CH2:20][N:19]([C:18]3[C:17]([C:32]#[N:33])=[CH:16][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)[CH2:18][CH2:17]2)[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 234980784-({3-chloro-4-[(1-methyl-1H-imidazol-2-yl)sulfanyl]phenyl}amino)-7-fluoro-6-(2-methoxyethoxy)-3-quinolinecarbonitrile

Product 1

HCID 86628426HCID 86628426, compound

Conditions

Temperature
105 °C

Procedure

Following the procedure of Example 11, a mixture of 150 mg (0.31 mmol) of 4-({3-chloro-4-[(1-methyl-1H-imidazole-2-yl)sulfanyl]phenyl}amino)-7-fluoro-6-(2-methoxyethoxy)-3-quinolinecarbonitrile and 287 mg (1.86 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 4:1 methylene chloride/methanol) gives 120 mg of 4-({3-chloro-4-[(1-methyl-1H-imidazole-2-yl)thio]phenyl}amino)-6-(2-methoxyethoxy)-7-(4-pyrrolidin-1-ylpiperidin-1-yl quinoline-3-carbonitrile as a yellow solid, mp 238-241° C.

Workup

  1. customto yield the crude product
  2. customPurification by silica gel chromatography (gradient 98:2 methylene chloride/methanol to 4:1 methylene chloride/methanol)

Sources & evidence

ORD record
ord-c24ec424337643af9ebe91b7c79e955e
Source dataset
uspto-grants-2010_08
Patent number
US07767671B2

Reaction notes

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