1-Methylpiperazine → HCID 10414315, compound

HRID 1837371Notes

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](F)=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[CH:18][C:17]=2[C:29]#[N:30])[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1.[CH3:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>CN1CCCC1=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([N:35]4[CH2:36][CH2:37][N:32]([CH3:31])[CH2:33][CH2:34]4)=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[CH:18][C:17]=2[C:29]#[N:30])[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of 200 mg (0.455 mmol) of 4-[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-7-fluoro-6-methoxyquinoline-3-carbonitrile (Reference Example 20) and 273 mg (2.73 mmol) of N-methylpiperazine in 1 mL of 1-methyl-2-pyrrolidinone was heated at 105° C. for 16 hours. The solvents are removed in vacuo. A 10 mL portion of water is added to the residue, from which a tan solid precipitates out. The solid is filtered off and washed with water. After drying in vacuo, the solid is suspended in ethyl acetate and stirred for 1 hour. The solid is filtered off, washed with ethyl acetate and dried in vacuo to provide 0.175 g of 4-[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-6-methoxy-7-(4-methypiperazin-1-yl)-quinoline-3-carbonitrile as a yellow solid, mp 270-272° C.

Workup

customThe solvents are removed in vacuo
additionA 10 mL portion of water is added to the residue, from which a tan solid
customprecipitates out
filtrationThe solid is filtered off
washwashed with water
customAfter drying in vacuo
filtrationThe solid is filtered off
washwashed with ethyl acetate
customdried in vacuo

Sources & evidence

ORD record: ord-b25ed8f5f48a40c6b15c49e8163d317e
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780996B2

Reaction notes

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