海萝胶 → N-[4-(2-carbamoyl-ethylamino)-3-nitro-phenyl]-N-methyl-benzamide

HRID 722410

反应方程式

HRID 722410 反应方程式
F[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:17])[C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].CCN(C(C)C)C(C)C.Cl.[NH2:31][CH2:32][CH2:33][C:34]([NH2:36])=[O:35].Cl>C(#N)C>[C:34]([CH2:33][CH2:32][NH:31][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:17])[C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19])(=[O:35])[NH2:36]

参与物

6

反应物 4

HCID 313海萝胶HCID 81531N,N-二异丙基乙胺HCID 11460004Benzamide, N-(4-fluoro-3-nitrophenyl)-N-methyl-HCID 22222288BETA-丙胺酰胺盐酸盐

产物 1

HCID 21884188N-[4-(2-carbamoyl-ethylamino)-3-nitro-phenyl]-N-methyl-benzamide

试剂、催化剂与溶剂 1

HCID 6342乙腈溶剂

反应条件

温度
80 °C

实验过程

N-(4-fluoro-3-nitro-phenyl)-N-methyl-benzamide (1.47 g, 5.37 mmol) was taken up in dry acetonitrile under argon, DIEA (2.08 g, 16.11 mmol, 2.80 ml) and β-alanine amide hydrochloride (1.00 g, 8.06 mmol) were added. The reaction mixture was heated to 80° C. for 48 h. The reaction was poured into 1N HCl and the aqueous layer was extracted 3× with ethyl acetate. The combined organic layers were washed with water, brine and dried over magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The residue was triturated twice with cold hexane and dried to give N-[4-(2-carbamoyl-ethylamino)-3-nitro-phenyl]-N-methyl-benzamide. (1.75 g, 95%)

后处理

  1. extractionthe aqueous layer was extracted 3× with ethyl acetate
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe solution was filtered
  5. customthe solvent removed under reduced pressure
  6. customThe residue was triturated twice with cold hexane
  7. customdried

来源与证据

ORD记录
ord-e834417c845e47c1acbbc78398a6df70
来源数据集
uspto-grants-2006_11
专利号
US07138420B2

关联笔记

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