Chlorosulfonyl isocyanate → 2-(2-Oxo-6-phenyl-3-ureido-2H-pyridin-1-yl)-N-(3,3,3-trifluoro-1-isopropyl-2-oxo-propyl)-acetamide

HRID 441200

Reaktionsgleichung

Reaktionsgleichung von HRID 441200
[NH2:1][C:2]1[C:3](=[O:28])[N:4]([CH2:14][C:15]([NH:17][CH:18]([CH:25]([CH3:27])[CH3:26])[C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])=[O:16])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.ClS([N:33]=[C:34]=[O:35])(=O)=O.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[O:28]=[C:3]1[C:2]([NH:1][C:34]([NH2:33])=[O:35])=[CH:7][CH:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]1[CH2:14][C:15]([NH:17][CH:18]([CH:25]([CH3:26])[CH3:27])[C:19](=[O:24])[C:20]([F:22])([F:23])[F:21])=[O:16]

Komponenten

6

Edukt 3

HCID 70918Chlorosulfonyl isocyanateHCID 516892Sodium BicarbonateHCID 102500732-(3-Amino-2-oxo-6-phenyl-2H-pyridin-1-yl)-N-(3,3,3-trifluoro-1-isopropyl-2-oxo-propyl)-acetamide

Produkt 1

HCID 99805542-(2-Oxo-6-phenyl-3-ureido-2H-pyridin-1-yl)-N-(3,3,3-trifluoro-1-isopropyl-2-oxo-propyl)-acetamideAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-(3-amino-2-oxo-6-phenyl-1,2-dihydro-1-pyridyl)-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (0.30 g) in tetrahydrofuran (5 mL), cooled to 0° C., was added, dropwise, chlorosulfonyl isocyanate (0.12 g). The reaction mixture was stirred for 10 min, neutralized with saturated aqueous sodium bicarbonate solution (1 mL), diluted with ethyl acetate (10 mL), and the organic phase washed (water, brine), dried (MgSO4) and evaporated. Purification by chromatography, using an eluant of methylene chloride:methanol (30:1), followed by overnight vacuum-drying (50° C. at 27 Pa), yielded the title product as a white solid (0.23 g); mp 227°-230° C. (dec); TLC: Rf =0.16, dichloromethane:methanol (20:1); 300 MHz NMR: 0.88 (2d,6), 2.15 (m,1), 4.50 (q,2), 4.65 (d,1), 6.18 (d,1), 6.40 (broad s,2), 7.40 (m,5), 8.08 (d,1), 8.35 (s,1), 8.75 (d,1); IR(KBr): 3470 (broad), 3360, 2980, 1760, 1700, 1535, 1490, 1210, 1160, 1020 cm-1 ; MS: m/z=439(M+1).

Aufarbeitung

  1. additionwas added
  2. washthe organic phase washed (water, brine)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customPurification by chromatography
  6. waitfollowed by overnight
  7. customvacuum-drying (50° C. at 27 Pa)

Quellen und Nachweise

ORD-Eintrag
ord-aeb1115342d94e89bbaa3784d99c19d4
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05521179

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