N-methyl-2-pyrrolidone → 6-Methoxy-4-[4-(pyridin-2-ylsulfanyl)-phenylamino]-7-(4-pyrrolidin-1-yl-piperidin-1-yl)quinoline-3-carbonitrile

HRID 269764Notes

Reaction equation

HRID 269764 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([S:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)=[CH:17][CH:16]=3)=[C:7]([C:12]#[N:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[O:28][CH3:29].[CH3:30][N:31]1[CH2:35][CH2:34][CH2:33][C:32]1=O>>[CH3:29][O:28][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:9]1[CH2:10][CH2:5][CH:30]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[CH2:7][CH2:8]1)[N:9]=[CH:8][C:7]([C:12]#[N:13])=[C:6]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 684614557-Fluoro-6-methoxy-4-[4-(pyridin-2-ylsulfanyl)-phenylamino]quinoline-3-carbonitrile

Product 1

HCID 684637256-Methoxy-4-[4-(pyridin-2-ylsulfanyl)-phenylamino]-7-(4-pyrrolidin-1-yl-piperidin-1-yl)quinoline-3-carbonitrile

Procedure

Following the procedure of Example 11, a mixture of 150 mg (0.37 mmol) of 7-fluoro-6-methoxy-4-[4-(pyridin-2-ylsulfanyl)-phenylamino]-quinoline-3-carbonitrile, 287 mg (1.86 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 107 mg of 6-methoxy-4-[4-(pyridin-2-ylsulfanyl)-phenylamino]-7-(4-pyrrolidin-1-yl-piperidin-1-yl)quinoline-3-carbonitrile as a yellow solid, mp 182-184° C.

Workup

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

Sources & evidence

ORD record
ord-fb8f7a44dda54c72906fe4a1278c0146
Source dataset
uspto-grants-2008_11
Patent number
US07449460B2

Reaction notes

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