2-Bromo-1-(thiophen-2-yl)ethan-1-one → 3-(Prop-2-ynyl)-8-(4-(thiophen-2-yl)thiazol-2-yl)imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-one

HRID 570924ノート

反応式

HRID 570924 の反応式
[O:1]=[C:2]1[N:7]([CH2:8][C:9]#[CH:10])[N:6]=[N:5][C:4]2=[C:11]([C:14](=[S:16])[NH2:15])[N:12]=[CH:13][N:3]12.Br[CH2:18][C:19]([C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)=O>CC#N>[CH2:8]([N:7]1[C:2](=[O:1])[N:3]2[CH:13]=[N:12][C:11]([C:14]3[S:16][CH:18]=[C:19]([C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)[N:15]=3)=[C:4]2[N:5]=[N:6]1)[C:9]#[CH:10]

参加物

4

反応物 2

HCID 27763722-Bromo-1-(thiophen-2-yl)ethan-1-oneHCID 498691414-Oxo-3-(prop-2-ynyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbothioamide

生成物 1

HCID 498706423-(Prop-2-ynyl)-8-(4-(thiophen-2-yl)thiazol-2-yl)imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-one収率 73%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

4-Oxo-3-(prop-2-ynyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbothioamide (0.43 mmol) and 2-bromo-1-(2-thienyl)-1-ethanone (0.43 mmol) were stirred in dry MeCN (2 mL) at room temperature overnight. A precipitate formed which was filtered off and treated with basic ion exchange resin. After removal of the resin, the liquor was recombined with the original filtrate and evaporated to dryness before being purified by column chromatography eluting with 5% MeCN/DCM to give the title compound. Yield 73%. δH (DMSO-d6) 8.95 (1H, s), 8.16 (1H, s) 7.67 (1H, dd, J=3.6, 1.2), 7.58 (1H, dd, J=4.8, 1.2), 7.16 (1H, dd, J=4.8, 3.6), 5.14 (2H, d, J=2.4), 3.53 (1H, t, J=2.4).

後処理

  1. customA precipitate formed which
  2. filtrationwas filtered off
  3. additiontreated with basic ion exchange resin
  4. customAfter removal of the resin
  5. customevaporated to dryness
  6. custombefore being purified by column chromatography
  7. washeluting with 5% MeCN/DCM

出典と根拠

ORDレコード
ord-2a86ef82ff9543bd876d44a759202d65
出典データセット
uspto-grants-2015_05
特許番号
US09024018B2

反応ノート

読み込み中…