4-(1-Pyrrolidinyl)piperidine → Balamapimod

HRID 499112Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 499112
[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.[N:31]1([CH:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH2:35][CH2:34][CH2:33][CH2:32]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:39]4[CH2:40][CH2:41][CH:36]([N:31]5[CH2:35][CH2:34][CH2:33][CH2:32]5)[CH2:37][CH2:38]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

Komponenten

4

Edukt 2

HCID 787034-(1-Pyrrolidinyl)piperidineHCID 234980744-[3-chloro-4-(1-methyl-1H-imidazole-2-ylsulfanyl)phenylamino]-7-fluoro-6-methoxyquinoline-3-carbonitrile

Produkt 1

HCID 11478684BalamapimodAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

A mixture of 150 mg (0.34 mmol) of 4-[3-chloro-4-(1-methyl-1H-imidazole-2-ylsulfanyl)-phenylamino]-7-fluoro-6-methoxyquinoline-3-carbonitrile and 316 mg (2.05 mmol) of 4-pyrrolidin-1-yl-piperidine in 1 mL of 1-methyl-2-pyrrolidinone is 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 is precipitated 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 140 mg of 4-[3-chloro-4-(1-methyl-1H-imidazole-2-ylsulfanyl)-phenylamino]-6-methoxy-7-(4-pyrrolidin-1-yl-piperidin-1-yl)quinoline-3-carbonitrile as a yellow solid, mp 225-229° C.

Aufarbeitung

  1. customThe solvents are removed in vacuo
  2. additionA 10 mL portion of water is added to the residue, from which a tan solid
  3. customis precipitated out
  4. filtrationThe solid is filtered off
  5. washwashed with water
  6. customAfter drying in vacuo
  7. filtrationThe solid is filtered off
  8. washwashed with ethyl acetate
  9. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-50e92d2bc9684c09ba9c050b8d50361f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767671B2

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