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

HRID 499114Notes

Reaction equation

HRID 499114 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([C:6](NC3C=CC(OC4C=NC=CC=4)=CC=3)=[C:7]([C:12]#[N:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1OC.[CH3:30][N:31]1[CH2:35][CH2:34][CH2:33][C:32]1=O>>[N:31]1([CH:30]2[CH2:5][CH2:10][N:9]([C:8]3[C:7]([C:12]#[N:13])=[CH:6][C:5]4[C:10](=[CH:11][CH:2]=[CH:3][CH:4]=4)[N:9]=3)[CH2:8][CH2:7]2)[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 684604217-Fluoro-6-methoxy-4-[4-(pyridin-3-yloxy)phenylamino]-quinoline-3-carbonitrile

Product 1

HCID 86628426HCID 86628426, compound

Procedure

Following the procedure of Example 11, a mixture of 150 mg (0.39 mmol) of 7-fluoro-6-methoxy-4-[4-(pyridin-3-yloxy)phenylamino]-quinoline-3-carbonitrile and 299 my (1.94 mmol) of 4-(1-pyrrolidinylpiperidine) are refluxed in 1-methyl 2-pyrrolidinone (1 mL) at 105° C. for 12 hours to yield the crude product. Purification by silica gel chromatography (95:5 methylene chloride/methanol) gives 120 my of 6-methoxy-4-[4-(pyridin-3-yloxy)phenylamino]-7-(4-pyrrolidin-1-yl-piperidin-1-ylquinoline-3-carbonitrile as a yellow solid, mp 194-196° C.

Workup

  1. customto yield the crude product
  2. customPurification by silica gel chromatography (95:5 methylene chloride/methanol)

Sources & evidence

ORD record
ord-3b6dd71b94a44bf3b5c05ba6c18e4435
Source dataset
uspto-grants-2010_08
Patent number
US07767671B2

Reaction notes

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