1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-Methyl-N-(tetrahydro-2H-pyran-4-yl)-[2,1,3]-benzothiadiazole-5-carboxamide

HRID 1951033

반응식

HRID 1951033 반응식
[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]

참가 물질

8

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6020112,1,3-Benzothiadiazole-5-carboxylic acidHCID 69919504-(Methylamino)tetrahydro-2H-pyran

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b504b6d774d149f78f34469d4f530d8b
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404682B2

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