Chloroacetone → 1-[(4-fluorophenyl)methyl]-N-[1-[2-[(4-methyl-2-thiazolyl)amino]ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine

HRID 979943Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 979943
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][NH:27][C:28]([NH2:30])=[S:29])[CH2:21][CH2:20]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:38][C:39](=O)[CH3:40]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[NH:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][NH:27][C:28]3[S:29][CH:38]=[C:39]([CH3:40])[N:30]=3)[CH2:21][CH2:20]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 13769777HCID 13769777, Verbindung

Produkt 1

HCID 137697091-[(4-fluorophenyl)methyl]-N-[1-[2-[(4-methyl-2-thiazolyl)amino]ethyl]-4-piperidinyl]-1H-benzimidazol-2-amineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred mixture of 4.3 parts of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]thiourea, 2.1 parts of potassium carbonate and 45 parts of tetrahydrofuran was added dropwise a solution of 0.9 parts of 1-chloro-2-propanone in a small amount of tetrahydrofuran. Upon completion, stirring at room temperature was continued overnight. The reaction mixture was filtered over Hyflo and the filtrate was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 3.8 parts (81%) of 1-[(4-fluorophenyl)methyl]-N-[1-[2-[(4-methyl-2-thiazolyl)amino]ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 184° C. (compound 85).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered over Hyflo
  2. customthe filtrate was evaporated
  3. customThe residue was crystallized from acetonitrile
  4. filtrationThe product was filtered off
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b1f97c517fd54d7aa4503d3ec7242b02
Quelldatensatz
uspto-grants-1987_01
Patentnummer
US04634704

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