Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 4-chloro-2-fluoro-5-[4-(3-fluorophenyl)-4-[2-[(1R,5S)-3-(2-methylbenzimidazol-1-yl)-8-azabicyclo[3.2.1]octan-8-yl]ethyl]piperidine-1-carbonyl]-N-propyl-benzenesulfonamide

HRID 1992138

Reaktionsgleichung

Reaktionsgleichung von HRID 1992138
FC1C=C(C2CCN([CH2:14][CH2:15][N:16]3[C@H:21]4[CH2:22][CH2:23][C@@H:17]3[CH2:18][CH:19]([N:24]3[C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=5[N:26]=[C:25]3[CH3:33])[CH2:20]4)CC2)C=CC=1.[Cl:34][C:35]1[CH:43]=[C:42]([F:44])[C:41]([S:45]([NH:48][CH2:49][CH2:50][CH3:51])(=[O:47])=[O:46])=[CH:40][C:36]=1[C:37]([OH:39])=O.CN(C(ON1N=N[C:62]2[CH:63]=[CH:64][CH:65]=[N:66][C:61]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[Cl:34][C:35]1[C:36]([C:37]([N:66]2[CH2:65][CH2:64][C:63]([C:40]3[CH:36]=[CH:35][CH:43]=[C:42]([F:44])[CH:41]=3)([CH2:14][CH2:15][N:16]3[C@H:17]4[CH2:23][CH2:22][C@@H:21]3[CH2:20][CH:19]([N:24]3[C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=5[N:26]=[C:25]3[CH3:33])[CH2:18]4)[CH2:62][CH2:61]2)=[O:39])=[CH:40][C:41]([S:45]([NH:48][CH2:49][CH2:50][CH3:51])(=[O:47])=[O:46])=[C:42]([F:44])[CH:43]=1

Komponenten

4

Edukt 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 587283362-Chloro-4-fluoro-5-[(propylamino)sulfonyl]benzoic acidHCID 686760111-((1R,5S)-8-{2-[4-(3-fluorophenyl)piperidinyl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole

Produkt 1

HCID 532610384-chloro-2-fluoro-5-[4-(3-fluorophenyl)-4-[2-[(1R,5S)-3-(2-methylbenzimidazol-1-yl)-8-azabicyclo[3.2.1]octan-8-yl]ethyl]piperidine-1-carbonyl]-N-propyl-benzenesulfonamideAusbeute 40 %

Versuchsvorschrift

0.366 g (0.82 mmol) 1-((1R,5S)-8-{2-[4-(3-fluorophenyl)piperidinyl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole and 0.363 g (1.23 mmol) 2-chloro-4-fluoro-5-[(propylamino)sulfonyl]benzoic acid were combined following the HATU general procedure in Example 5. This compound was purified by flash chromatography on a 0-100% gradient of 90:5:5 acetonitrile: ammonium hydroxide: water in acetonitrile. 0.24 g obtained (40% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.04-8.15 (br, 1H), 7.69-7.90 (m, 2H), 7.32-7.52 (m, 3H), 7.19-7.26 (m, 2H), 7.01-7.15 (m, 3H), 4.41-4.56 (m, 1H), 3.86-3.98 (m, 1H), 3.19-3.43 (m, 6H), 2.97-3.08 (m, 1H), 2.77-2.88 (m, 2H), 2.44 (s, 3H), 2.28-2.41 (m, 2H), 1.96-2.17 (m, 2H), 1.71-1.92 (m, 9H), 1.56-1.64 (m, 2H), 1.31-1.42 (m, 2H), 0.73-0.81 (m, 3H).

Aufarbeitung

  1. customThis compound was purified by flash chromatography on a 0-100% gradient of 90:5:5 acetonitrile
  2. custom0.24 g obtained (40% yield)

Quellen und Nachweise

ORD-Eintrag
ord-47343633659d494ba9822c5023541ab9
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07645771B2

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