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

反応式

HRID 441200 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-aeb1115342d94e89bbaa3784d99c19d4
出典データセット
uspto-grants-1996_05
特許番号
US05521179

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