Methyl N-(triethylammoniosulfonyl)carbamate → Tert-butyl 1-(6-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate

HRID 1616065ノート

反応式

HRID 1616065 の反応式
[C:1]([NH:4][NH:5][C:6]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=2)[N:11]=[C:10]([CH:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH3:20])[C:9]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)=O)(=[O:3])[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>ClC(Cl)C.O>[F:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH:19]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:27])[CH3:26])[CH3:20])[C:9]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)=[C:8]2[C:6]1[O:3][C:1]([CH3:2])=[N:4][N:5]=1

参加物

5

反応物 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 67595345Tert-butyl 1-(4-(2-acetylhydrazinecarbonyl)-6-fluoro-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate

生成物 1

HCID 67595696Tert-butyl 1-(6-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 63651,1-Dichloroethane溶媒

実験手順

A solution of tert-butyl 1-(4-(2-acetylhydrazinecarbonyl)-6-fluoro-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate (0.553 g, 1.183 mmol) and Burgess reagent (1.128 g, 4.73 mmol) in dichloroethane (11.83 mL) was heated in the microwave at 120° C. for 1 h. The reaction mixture was diluted with water (50 mL) and extracted with DCM (2×50 mL). The organic extracts were washed with brine (1×50 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give the crude product. The crude material was purified by silica gel column chromatography eluting with a gradient of 0% to 100% EtOAc in hexane, to provide tert-butyl 1-(6-fluoro-4-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(pyridin-2-yl)quinolin-2-yl)ethylcarbamate as a pink solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.61 (1H, d, J=4.3 Hz), 8.22-8.32 (1H, m), 7.80-7.92 (3H, m), 7.36-7.49 (2H, m), 7.17 (1H, d, J=7.0 Hz), 4.88 (1H, t, J=7.1 Hz), 2.34 (3H, s), 1.22-1.38 (12H, m); LC-MS (ESI) m/z 450.1 [M+H]+.

後処理

  1. extractionextracted with DCM (2×50 mL)
  2. washThe organic extracts were washed with brine (1×50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customThe crude material was purified by silica gel column chromatography
  8. washeluting with a gradient of 0% to 100% EtOAc in hexane

出典と根拠

ORDレコード
ord-395d0a699e74407c9df70f739da533e8
出典データセット
uspto-grants-2014_07
特許番号
US08765768B2

反応ノート

読み込み中…