2-(Methylthio)thiazolo[5,4-b]pyridine → N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]thiazolo[5,4-b]pyridin-2-amine

HRID 893688

Reaktionsgleichung

Reaktionsgleichung von HRID 893688
CS[C:3]1[S:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][N:6]=2.[NH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]2[N:26]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[C:25]3[CH:35]=[CH:36][CH:37]=[CH:38][C:24]=3[N:23]=2)[CH2:17][CH2:16]1>>[F:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][N:26]2[C:25]3[CH:35]=[CH:36][CH:37]=[CH:38][C:24]=3[N:23]=[C:22]2[NH:21][CH:18]2[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][NH:12][C:3]3[S:4][C:5]4[C:10]([N:11]=3)=[CH:9][CH:8]=[CH:7][N:6]=4)[CH2:16][CH2:17]2)=[CH:29][CH:30]=1

Komponenten

3

Edukt 2

HCID 6998402-(Methylthio)thiazolo[5,4-b]pyridineHCID 12891741N-[1-(2-aminoethyl)-4-piperidinyl]-1-(4-fluorophenylmethyl)-1H-benzimidazol-2-amine

Produkt 1

HCID 13983104N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]thiazolo[5,4-b]pyridin-2-amineAusbeute 25 %

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 2.8 parts of 2-(methylthio)thiazolo[5,4-b]pyridine and 5.5 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-amine was stirred for 24 hours at 140° C. The reaction mixture was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 1.9 parts (25%) of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]thiazolo[5,4-b]pyridin-2-amine; mp. 203.5° C. (compound 103).

Aufarbeitung

  1. customThe reaction mixture was purified by column chromatography over silica gel using
  2. additiona mixture of trichloromethane and methanol
  3. customThe pure fractions were collected
  4. customthe eluent was evaporated
  5. customThe residue was crystallized from acetonitrile
  6. filtrationThe product was filtered off
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-35d0caf21eae44f48453a1f3d354853d
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05126339

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