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5-hydrazinyl-1-methyl-1H-pyrazole → 4-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-(1-methyl-1H-pyrazol-5-yl)-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one

HRID 873981
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 873981
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([C:13]3[CH:14]=[C:15]([CH3:23])[C:16]4[N:17]([C:19]([CH3:22])=[N:20][N:21]=4)[CH:18]=3)[C:11](=[O:24])[C:10](O)=[C:9]2[C:26]([CH:28]2[CH2:30][CH2:29]2)=O)=[CH:4][CH:3]=1.[NH:31]([C:33]1[N:37]([CH3:38])[N:36]=[CH:35][CH:34]=1)[NH2:32]>CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:9]3[C:26]([CH:28]4[CH2:29][CH2:30]4)=[N:32][N:31]([C:33]4[N:37]([CH3:38])[N:36]=[CH:35][CH:34]=4)[C:10]=3[C:11](=[O:24])[N:12]2[C:13]2[CH:14]=[C:15]([CH3:23])[C:16]3[N:17]([C:19]([CH3:22])=[N:20][N:21]=3)[CH:18]=2)=[CH:4][CH:3]=1
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Komponenten

4

Edukt 2

HCID 684257025-hydrazinyl-1-methyl-1H-pyrazoleHCID 1177026275-(4-chlorophenyl)-4-(cyclopropanecarbonyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]-pyridin-6-yl)-3-hydroxy-1H-pyrrol-2(5H)-one

Produkt 1

HCID 862927794-(4-chlorophenyl)-3-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-1-(1-methyl-1H-pyrazol-5-yl)-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283
Diethyl Ether
Lösungsmittel

Versuchsvorschrift

The title compound was prepared in analogy to the procedure described in Step 114.1 using 5-(4-chlorophenyl)-4-(cyclopropanecarbonyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-hydroxy-1H-pyrrol-2(5H)-one (Step 117.1) and 5-hydrazinyl-1-methyl-1H-pyrazole (Step 74.2). The crude material was first purified by silica gel column chromatography (1% ammonia/5% MeOH/CH2Cl2) followed by preparative achiral SFC (column Silica, gradient 23-28% in 6 min_total 11 min). A third purification was performed by preparative HPLC (Gilson gx-281. Column: Sunfire C18, 30×100 mm, 5 mm. Flow: 30 mL/min. Gradient: 30% to 60% B in min; A=0.1% TFA in H2O, B=CH3CN. Detection: UV). The fractions were combined, basified with NaHCO3, the CH3CN was removed under reduced pressure and the resulting aqueous layer was extracted with CH2Cl2, the organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford, after trituration in Et2O, a white solid. tR: 0.99 min (LC-MS 2); ESI-MS: 499 [M+H]+ (LC-MS 2); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.03-0.14 (m, 1H) 0.67-0.80 (m, 2H) 0.80-0.92 (m, 1H) 1.78-1.85 (m, 1H) 2.42 (s, 3H) 2.61 (s, 3H) 3.85 (s, 3H) 6.55 (s, 1H) 6.63 (d, J=2.0 Hz, 1H) 7.30 (s, 1H) 7.37 (d, J=8.6 Hz, 2H) 7.46 (d, J=8.6 Hz, 2H) 7.56 (d, J=1.6 Hz, 1H) 8.39 (s, 1H).

Aufarbeitung

  1. customThe crude material was first purified by silica gel column chromatography (1% ammonia/5% MeOH/CH2Cl2)
  2. customfollowed by preparative achiral SFC (column Silica, gradient 23-28% in 6 min_total 11 min)
  3. customA third purification
  4. customthe CH3CN was removed under reduced pressure
  5. extractionthe resulting aqueous layer was extracted with CH2Cl2
  6. washthe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-f1d3253e6f2f4ae6b08868de83902e41
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08975417B2

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