2-Butanamine, 2-methyl- → (1Z)-1-[3-(2-methoxyethyl)-4,5-dimethyl-1,3-thiazol-2-ylidene]-3-(2-methylbutan-2-yl)urea

HRID 78456

反応式

HRID 78456 の反応式
[CH3:1][C:2]([NH2:6])([CH3:5])[CH2:3][CH3:4].Cl[C:8](OC1C=CC([N+]([O-])=O)=CC=1)=[O:9].Br.[CH3:21][O:22][CH2:23][CH2:24][N:25]1[C:29]([CH3:30])=[C:28]([CH3:31])[S:27][C:26]1=[NH:32]>C1COCC1.C(N(CC)C(C)C)(C)C>[CH3:1][C:2]([NH:6][C:8](/[N:32]=[C:26]1\[S:27][C:28]([CH3:31])=[C:29]([CH3:30])[N:25]\1[CH2:24][CH2:23][O:22][CH3:21])=[O:9])([CH3:5])[CH2:3][CH3:4]

参加物

6

反応物 3

HCID 689862-Butanamine, 2-methyl-HCID 821294-Nitrophenyl chloroformateHCID 668517223-(2-Methoxyethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine hydrobromide

生成物 1

HCID 87518902(1Z)-1-[3-(2-methoxyethyl)-4,5-dimethyl-1,3-thiazol-2-ylidene]-3-(2-methylbutan-2-yl)urea

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 81531Diisopropylethylamine溶媒

実験手順

To a solution of 1,1-dimethylpropylamine (174 mg, 2.0 mmole) in 19 mL of THF and 1 mL of N,N-diisopropylethyl amine was added 4-nitrophenyl chloroformate (403 mg, 2.0 mmole). The solution was irradiated in a sealed tube placed in a single node microwave at 70° C. for 300 sec (maximum power 300 W) with stirring. The resulting solution was cooled to room temperature and 3-(2-methoxyethyl)-4,5-dimethyl-3H-thiazol-2-ylideneamine hydrobromide (587 mg, 2.2 mmole) from Example 12A was added. The sealed tube was irradiated at 120° C. for 1800 sec with stirring. The mixture was cooled and the volatile components were removed under reduced pressure. The residue was partitioned between water and ethyl acetate. The phases were separated and organic extract was dried over anhydrous Na2SO4, filtered, and concentrated. Purification by column chromatography (SiO2, 0-70% ethyl acetate/hexanes gradient) afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.76 (t, J=7 Hz, 3H) 1.20 (s, 6H) 1.66 (d, J=7 Hz, 2H) 2.06 (s, 3H) 2.11 (s, 3H) 3.30 (s, 3H) 3.55 (t, J=5 Hz, 2H) 4.06 (t, J=5 Hz, 2H) 6.13 (s, 1H)), MS (DCI/NH3) m/z 300 (M+H)+.

後処理

  1. customThe solution was irradiated in a sealed tube
  2. customThe sealed tube was irradiated at 120° C. for 1800 sec
  3. stirringwith stirring
  4. temperatureThe mixture was cooled
  5. customthe volatile components were removed under reduced pressure
  6. customThe residue was partitioned between water and ethyl acetate
  7. customThe phases were separated
  8. extractionorganic extract
  9. dry with materialwas dried over anhydrous Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customPurification by column chromatography (SiO2, 0-70% ethyl acetate/hexanes gradient)

出典と根拠

ORDレコード
ord-0e1352d51a534e9e9737731e63271971
出典データセット
uspto-grants-2014_09
特許番号
US08841334B2

関連ノート

読み込み中…