Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 4-chloro-N-cyclopropyl-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]benzenesulfonamide

HRID 1992142

Reaktionsgleichung

Reaktionsgleichung von HRID 1992142
[F:1][C:2]1[CH:3]=[C:4]([C:8]2([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)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[Cl:34][C:35]1[CH:43]=[C:42]([F:44])[C:41]([S:45]([NH:48][CH:49]2[CH2:51][CH2:50]2)(=[O:47])=[O:46])=[CH:40][C:36]=1[C:37](O)=[O:38].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[Cl:34][C:35]1[C:36]([C:37]([N:11]2[CH2:10][CH2:9][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)([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)[CH2:13][CH2:12]2)=[O:38])=[CH:40][C:41]([S:45]([NH:48][CH:49]2[CH2:51][CH2:50]2)(=[O:46])=[O:47])=[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 587283292-Chloro-4-fluoro-5-[(cyclopropylamino)sulfonyl]benzoic acidHCID 587288151-((1R,5S)-8-{2-[4-(3-fluorophenyl)piperidin-4-yl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole

Produkt 1

HCID 532608894-chloro-N-cyclopropyl-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]benzenesulfonamideAusbeute 43 %

Versuchsvorschrift

0.335 g (0.75 mmol) 1-((1R,5S)-8-{2-[4-(3-fluorophenyl)piperidin-4-yl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole and 0.242 g (0.83 mmol) 2-chloro-4-fluoro-5-[(cyclopropylamino)sulfonyl]benzoic acid were combined following the HATU general procedure in Example 5. This compound was purified by reverse phase chromatography on a 0-100% gradient of 0.1% TFA in water in acetonitrile. 0.231 g obtained (43% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.38-8.47 (br, 1H), 7.72-7.92 (m, 2H), 7.33-7.51 (m, 3H), 7.20-7.28 (m, 2H), 7.01-7.16 (m, 3H), 4.45-4.57 (m, 1H), 4.06-4.12 (m, 1H), 3.87-3.98 (m, 1H), 3.21-3.42 (m, 6H), 2.97-3.10 (m, 1H), 2.44 (s, 3H), 2.23-2.42 (m, 2H), 1.95-2.17 (m, 2H), 1.72-1.92 (m, 8H), 1.55-1.65 (m, 2H), 0.34-0.53 (m, 4H).

Aufarbeitung

  1. customThis compound was purified by reverse phase chromatography on a 0-100% gradient of 0.1% TFA in water in acetonitrile
  2. custom0.231 g obtained (43% yield)

Quellen und Nachweise

ORD-Eintrag
ord-95015999d27d4718a0055b4314e2502b
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07645771B2

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