1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 → N-Methyl-N-(tetrahydro-2H-pyran-4-yl)-[2,1,3]-benzothiadiazole-5-carboxamide

HRID 906681

反应方程式

HRID 906681 反应方程式
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[N:9]1[S:10][N:11]=[C:12]2[CH:17]=[C:16]([C:18](O)=[O:19])[CH:15]=[CH:14][C:13]=12.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.CN(C=O)C.C(N(CC)CC)C>[CH3:1][N:2]([CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)[C:18]([C:16]1[CH:15]=[CH:14][C:13]2=[N:9][S:10][N:11]=[C:12]2[CH:17]=1)=[O:19]

参与物

8

反应物 4

HCID 159081-(3-二甲基氨基丙基)-3-乙基碳二亚胺HCID 757711-羟基苯并三唑(HOBT)HCID 6020112,1,3-苯并噻二唑-5-甲酸HCID 6991950N-甲基四氢-2H-吡喃-4-胺

产物 1

HCID 25104408N-Methyl-N-(tetrahydro-2H-pyran-4-yl)-[2,1,3]-benzothiadiazole-5-carboxamide

试剂、催化剂与溶剂 3

HCID 142844-二甲氨基吡啶(DMAP)催化剂HCID 6228N,N-二甲基甲酰胺溶剂HCID 8471三乙胺溶剂

实验过程

N-Methyltetrahydro-2H-pyran-4-amine (0.4 g, 3.4 mmol), [2,1,3]-benzothiadiazole-5-carboxylic acid (0.23 g, 1.4 mmol), DMAP (0.2 g: 1.6 mmol), HOBT (0.2 g, 1.5 mmol), triethylamine (1.0 ml) and EDCI (1 g, 6.4 mmol) were dissolved in DMF (30 ml). The mixture was stirred at room temperature for 18 h and then concentrated under vacuum. Chloroform (100 ml) was added and the mixture washed with water (100 ml) and H2SO4 (→pH 2) and NaHCO3 solution (100 ml). The aqueous was extracted with chloroform (100 ml) and the combined organics were dried (MgSO4), concentrated under vacuum, and the crude product was purified on a silica gel column eluting with chloroform/THF (90:10), to give the product as an oil which crystallized on standing. Mp=106-108° C., 1H NMR (300 MHz, CDCl3, rotamers) δ 8.06 (d, J=9.0 Hz, 1H); 8.01 (s, 1H); 7.60 (d, J=9.0 Hz, 1H); 4.92-4.75 and 4.15-3.10 (m, 5H); 3.10-2.80 (m, 3H) and 2.05-1.50 ppm (s, 4H).

后处理

  1. concentrationconcentrated under vacuum
  2. additionChloroform (100 ml) was added
  3. washthe mixture washed with water (100 ml) and H2SO4 (→pH 2) and NaHCO3 solution (100 ml)
  4. extractionThe aqueous was extracted with chloroform (100 ml)
  5. dry with materialthe combined organics were dried (MgSO4)
  6. concentrationconcentrated under vacuum
  7. customthe crude product was purified on a silica gel column
  8. washeluting with chloroform/THF (90:10)

来源与证据

ORD记录
ord-3b7ee58a101d430280d12cda2d36b418
来源数据集
uspto-grants-2011_09
专利号
US08013003B2

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