Hydrochloric Acid → 4-Iodo-3-(2-methyl-acryloylamino)-benzoic acid methyl ester

HRID 1053729

反応式

HRID 1053729 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[I:12])[C:5]([O:7][CH3:8])=[O:6].[C:13](O)(=[O:17])[C:14]([CH3:16])=[CH2:15].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl>ClCCl.CN(C=O)C>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][C:11]([I:12])=[C:2]([NH:1][C:13](=[O:17])[C:14]([CH3:16])=[CH2:15])[CH:3]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 4093Methacrylic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21628210Methyl 3-amino-4-iodobenzoate

生成物 1

HCID 684823374-Iodo-3-(2-methyl-acryloylamino)-benzoic acid methyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

To a stirred suspension of Methyl 3-amino-4-iodobenzoate (1.67 g, 6 mmol) and Methacrylic acid (568 mg, 6.6 mmol) in dichloromethane (60 mL) and DMF (60 mL) were added O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (2.5 g, 6.6 mmol) and then a solution of N,N-diisopropylethylamine (1.16 g, 1560 μL, 9 mmol) in DMF (20 mL). The reaction mixture was stirred at ambient temperature for 24 h. The reaction medium was acidified by adding a 1.2 M hydrochloric acid solution and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4), and concentrated to give the amide which was purified by flash chromatography (AcOEt/heptane: 5/5).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-e36ba10e1d384ecf932dd1f9042ce4aa
出典データセット
uspto-grants-2016_07
特許番号
US09394267B2

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