Diisopropylethylamine → E-3-[3'-chloro-4'-hydroxybiphenyl-4-yl]-N-hydroxy-acrylamide

HRID 12989

反応式

HRID 12989 の反応式
[Cl:1][C:2]1[CH:3]=[C:4](/[C:9](=[CH:13]\[C:14]2C=CC=CC=2)/[C:10](O)=O)[CH:5]=[CH:6][C:7]=1[OH:8].CN(C([O:27][N:28]1N=N[C:30]2[CH:31]=[CH:32][CH:33]=N[C:29]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.N[OH:55]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:33][C:32](/[CH:31]=[CH:30]/[C:29]([NH:28][OH:27])=[O:55])=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[OH:8]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68583309E-3-chloro-4-hydroxyphenylcinnamic acid

生成物 1

HCID 15986507E-3-[3'-chloro-4'-hydroxybiphenyl-4-yl]-N-hydroxy-acrylamide収率 9.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

205 mg (0.75 mmol) of E-3-chloro-4-hydroxyphenylcinnamic acid were dissolved under nitrogen in 7.5 ml of DMF, then 285 mg (0.75 mmol) of HATU and 97 μL (0.56 mmol) of DIPEA were added and the solution thus obtained was kept under stirring at room temperature for 2 min. After addition of hydroxylamine hydrochloride (261 mg, 3.75 mmol), the mixture was stirred at room temperature for 2 days. DMF was removed under reduced pressure and the residue was washed with water to obtain, after filtration, 140 mg of a crude product. Purification by flash chromatography on reverse phase ((LiChroprep RP-18, MERCK) using as eluent water/methanol 1:1 and crystallization from diethyl ether afforded 21 mg of the title compound as a white solid. M.p. 172-175° C. Rf=0.16 (RP18 MERCK, H2O/MeOH 1:1).

後処理

  1. customthe solution thus obtained
  2. stirringthe mixture was stirred at room temperature for 2 days
  3. customDMF was removed under reduced pressure
  4. washthe residue was washed with water
  5. customto obtain
  6. filtrationafter filtration, 140 mg of a crude product
  7. customPurification by flash chromatography on reverse phase ((LiChroprep RP-18, MERCK)
  8. customwater/methanol 1:1 and crystallization from diethyl ether

出典と根拠

ORDレコード
ord-4f92bbdf0eb249bf94c24643ff3d3a30
出典データセット
uspto-grants-2010_06
特許番号
US07728039B2

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