2-Bromo-5-nitrothiazole → 2,2-Dimethyl-4-{4'-[(5-nitro-1,3-thiazol-2-yl)amino]-1,1'-biphenyl-4-yl}-4-oxobutanoic acid

HRID 30916

反応式

HRID 30916 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:22])[CH2:15][C:16]([CH3:21])([CH3:20])[C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Br[C:24]1[S:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][N:28]=1>C(O)CCC>[CH3:21][C:16]([CH3:20])([CH2:15][C:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:24]3[S:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][N:28]=3)=[CH:7][CH:6]=2)=[CH:9][CH:10]=1)=[O:22])[C:17]([OH:19])=[O:18]

参加物

4

反応物 2

HCID 182112-Bromo-5-nitrothiazoleHCID 219856934-[4-(4-Aminophenyl)phenyl]-2,2-dimethyl-4-oxobutanoic acid

生成物 1

HCID 116690542,2-Dimethyl-4-{4'-[(5-nitro-1,3-thiazol-2-yl)amino]-1,1'-biphenyl-4-yl}-4-oxobutanoic acid収率 10.5%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
90 °C

実験手順

In a 8-mL screw-cap vial, a mixture of 4-(4′-amino-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoic acid (60 mg, 0.20 mmol) and 2-bromo-5-nitro-1,3-thiazole (63.3 mg, 0.30 mmol) in 4 mL n-butanol was heated at 90° C. overnight. The solvent was removed under reduced pressure. The mixture was dissolved in 5 mL 1:4 MeOH/DMF and purified by reverse-phase HPLC to provide 8.9 mg (10%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 11.55 (br s, 1H), 8.50 (s, 11H), 7.70-8.05 (m, 8H), 3.15 (d, 1H), 1.25 (s, 6H); LC-MS m/z 426.2 (MH+), ret. time 3.12 min.

後処理

  1. customIn a 8-mL screw-cap vial
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe mixture was dissolved in 5 mL 1:4 MeOH/DMF
  4. custompurified by reverse-phase HPLC

出典と根拠

ORDレコード
ord-14e91ff12c264674828bc4bf2dcfc794
出典データセット
uspto-grants-2008_09
特許番号
US07423156B2

関連ノート

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