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Triethylamine → HCID 91826344, Verbindung

HRID 874002
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 874002
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:15]3[C:14]([CH3:16])=[N:13][NH:12][C:11]=3[C:10](=[O:17])[N:9]2[C:18]2[CH:23]=[C:22]([CH3:24])[C:21](=[O:25])[N:20]([CH3:26])[CH:19]=2)=[CH:4][CH:3]=1.[CH3:27][NH:28][C:29](N1C=CN=C1)=[O:30].C(N(CC)CC)C>C(Cl)Cl.C(Cl)Cl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:15]3[C:11](=[N:12][N:13]([C:29]([NH:28][CH3:27])=[O:30])[C:14]=3[CH3:16])[C:10](=[O:17])[N:9]2[C:18]2[CH:23]=[C:22]([CH3:24])[C:21](=[O:25])[N:20]([CH3:26])[CH:19]=2)=[CH:4][CH:3]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:15]3[C:14]([CH3:16])=[N:13][N:12]([C:29]([NH:28][CH3:27])=[O:30])[C:11]=3[C:10](=[O:17])[N:9]2[C:18]2[CH:23]=[C:22]([CH3:24])[C:21](=[O:25])[N:20]([CH3:26])[CH:19]=2)=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 12420700N-methyl-1H-imidazole-1-carboxamide2×HCID 178434165HCID 178434165, Verbindung

Produkt 2

HCID 91826344HCID 91826344, VerbindungHCID 91826345HCID 91826345, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 21908982Water methylene chlorideLösungsmittel

Versuchsvorschrift

A mixture of 4-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Example 27) (150 mg, 0.407 mmol), N-methyl-1H-imidazole-1-carboxamide [Duspara, Petar A.; Islam, Md. Sadequl; Lough, Alan J.; Batey, Robert A. Journal of Organic Chemistry (2012), 77(22), 10362-10368] (50.9 mg, 0.407 mmol) and triethylamine (0.057 mL, 0.407 mmol) in CH2Cl2 (4 mL) was stirred for 16 h at rt. N-methyl-1H-imidazole-1-carboxamide (50 mg) was added. The reaction mixture was stirred for 3 days at rt, diluted with CH2Cl2/water and extracted twice with CH2Cl2. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by chromatography (1% ammonia/5% MeOH/DCM), subsequent preparative achiral SFC (column: Reprosil 70 NH2, 250×30 mm, 5 μm, Dr Maisch; eluent: MeOH/scCO2; gradient: 1 min 21% MeOH, 21-26% MeOH in 6 min, 26-50% MeOH, in 1 min, 1.5 min 50% MeOH; flow: 100 mL/min) and trituration of the resulting products in diethyl ether to afford 57 mg of 4-(4-chlorophenyl)-5-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-N,3-dimethyl-6-oxo-5,6-dihydropyrrolo[3,4-c]pyrazole-2(4H)-carboxamide (Example 144) and 26 mg of the title compound. tR: 0.84 min (LC-MS 2); ESI-MS: 426.1 [M+H]+ (LC-MS 2); Rf=0.24 (NH3 1%/CH2Cl2/MeOH 5%); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.92 (s, 3H) 1.98 (s, 3H) 2.83 (d, J=4.30 Hz, 3H) 3.35 (s, 3H) 6.17 (s, 1H) 7.26-7.45 (m, 5H) 7.74 (br. s., 1H) 8.53 (d, J=4.30 Hz, 1H).

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 3 days at rt
  2. extractionextracted twice with CH2Cl2
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (1% ammonia/5% MeOH/DCM), subsequent preparative achiral SFC (column: Reprosil 70 NH2, 250×30 mm, 5 μm, Dr Maisch; eluent: MeOH/scCO2; gradient: 1 min 21% MeOH, 21-26% MeOH in 6 min, 26-50% MeOH, in 1 min, 1.5 min 50% MeOH; flow: 100 mL/min) and trituration of the resulting products in diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-660cd3c690d2455f945c6cd86d8e2d17
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08975417B2

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