对氨基苯甲酸 → 4-amino-N-methyl-N-(2-pyridin-2-ylethyl)benzamide

HRID 17833

反应方程式

HRID 17833 反应方程式
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[CH3:11][NH:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:12]([CH3:11])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[O:8])=[CH:9][CH:10]=1

参与物

6

反应物 4

HCID 978对氨基苯甲酸HCID 2366倍他司汀HCID 81531N,N-二异丙基乙胺HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

产物 1

HCID 283991514-amino-N-methyl-N-(2-pyridin-2-ylethyl)benzamide

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

p-Aminobenzoic acid (1 g, 0.0073 mol) was dissolved in DMF (15 ml), methyl-(2-pyridin-2-yl-ethyl)amine (5 ml, 5 eq) was added, followed by DIPEA (1.91 ml, 1.5 eq), and HATU (4.1 g, 1.5 eq). After stirring for 3 h, TLC showed complete consumption of starting material. Water was added and the mixture extracted with CH2Cl2, the organic extracts were washed with NaHCO3 (sat), NH4Cl (sat), dried (MgSO4), concentrated under reduced pressure, and purified by flash chromatography (SiO2, EtOAc-EtOAc/MeOH 95:5) to give 1.43 g of 4-amino-N-methyl-N-(2-pyridin-2-ylethyl)benzamide. Step B: Preparation 1B (100 mg, 0.371 mmol) and the product of step A (142 mg, 1.5 eq) were dissolved in DMF (2 ml), potassium tert-butoxide (91 mg, 2.2 eq) was added and the mixture allowed to stir overnight. Water was added and the mixture extracted with EtOAc, dried (MgSO4), concentrated under reduced pressure, and the residue purified by flash chromatography (SiO2, hexane-EtOAc) to give 56 mg of the title compound. LCMS: MH+=489.3.

后处理

  1. customconsumption of starting material
  2. additionWater was added
  3. extractionthe mixture extracted with CH2Cl2
  4. washthe organic extracts were washed with NaHCO3 (sat), NH4Cl (sat)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. custompurified by flash chromatography (SiO2, EtOAc-EtOAc/MeOH 95:5)

来源与证据

ORD记录
ord-9278e2e1590149b49e3719679cf90bb5
来源数据集
uspto-grants-2010_06
专利号
US07741318B2

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