Methylamine → 5-(1H-indol-5-yl)-N-methyl-1,3,4-thiadiazol-2-amine

HRID 634151노트

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HRID 634151 반응식
CS([C:5]1[S:9][C:8]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15](C([O-])=O)[CH:14]=[CH:13]3)=[N:7][N:6]=1)(=O)=O.[CH3:22][NH2:23].CCOC(C)=O>CS(C)=O>[NH:15]1[C:16]2[C:12](=[CH:11][C:10]([C:8]3[S:9][C:5]([NH:23][CH3:22])=[N:6][N:7]=3)=[CH:18][CH:17]=2)[CH:13]=[CH:14]1

참가 물질

5

반응물 3

HCID 6329MethylamineHCID 8857Ethyl AcetateHCID 867250995-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)-1H-indole-1-carboxylate

생성물 1

HCID 683279525-(1H-indol-5-yl)-N-methyl-1,3,4-thiadiazol-2-amine수율 78%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
110 °C

실험 절차

To a mixture of 5-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)-1H-indole-1-carboxylate (8 g, 21.11 mmol) in a sealed tube was added methylamine in DMSO (80 mL). The reaction was heated at 110° C. for 1 h and ice-cold water and EtOAc was added. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried, filtered and concentrated. The residue was purified with silica gel chromatography (eluting with 40% EtOAc in Hex) to give 5-(1H-indol-5-yl)-N-methyl-1,3,4-thiadiazol-2-amine (3.8 g, 78%). MS (ESI, pos. ion) m/z: 231 (M+1); 1H-NMR (DMSO-d6, 300 MHz): δ ppm 2.9 (s, 3H), 6.5 (d, 1H) 7.4 (d, 3H) 7.8 (m, 1H), 7.9 (s, 1H), 11.4 (s, 1H).

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel chromatography (eluting with 40% EtOAc in Hex)

출처 및 근거

ORD 기록
ord-d3197d52fd7a46fdbf573e6ad9d5ebbe
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321756B2

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