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

Reaction equation

HRID 441200 reaction equation
[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]

Participants

6

Reactant 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

Product 1

HCID 99805542-(2-Oxo-6-phenyl-3-ureido-2H-pyridin-1-yl)-N-(3,3,3-trifluoro-1-isopropyl-2-oxo-propyl)-acetamideYield 69.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-aeb1115342d94e89bbaa3784d99c19d4
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Linked notes

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