Triethylamine → Losulazine

HRID 1863016Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1863016
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:27]=[CH:26][C:17]([C:18]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)=[O:19])=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[F:37][C:38]1[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][CH:39]=1>O1CCCC1>[F:37][C:38]1[CH:43]=[CH:42][C:41]([S:44]([N:23]2[CH2:24][CH2:25][N:20]([C:18](=[O:19])[C:17]3[CH:26]=[CH:27][C:14]([NH:13][C:7]4[C:6]5[C:11](=[CH:12][C:3]([C:2]([F:1])([F:28])[F:29])=[CH:4][CH:5]=5)[N:10]=[CH:9][CH:8]=4)=[CH:15][CH:16]=3)[CH2:21][CH2:22]2)(=[O:46])=[O:45])=[CH:40][CH:39]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 30552431-Piperazinyl(4-((7-(trifluoromethyl)-4-quinolinyl)amino)phenyl)methanone

Produkt 1

HCID 54750LosulazineAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of 4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine (2 g, 0.005 mol) and 0.5 g of triethylamine in 30 ml of tetrahydrofuran is added dropwise a solution of p-fluorophenylsulfonyl chloride in 10 ml of tetrahydrofuran over a 15 minute period. After complete addition, the resultant mixture is stirred for 1 hour at room temperature. The resulting mixture is filtered and the white solid is washed with more tetrahydrofuran and dried. This is re-crystallized from methanol/methylene chloride to give 2.5 g (92%) of white crystalline 1-[(4-fluorophenyl)sulfonyl]-4-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperazine of melting point 251°-253° C.

Aufarbeitung

  1. additionAfter complete addition
  2. filtrationThe resulting mixture is filtered
  3. washthe white solid is washed with more tetrahydrofuran
  4. customdried
  5. customThis is re-crystallized from methanol/methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-94473fa4afa64f2b8241f22ac0e988b9
Quelldatensatz
uspto-grants-1979_09
Patentnummer
US04167567

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