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 570924노트

반응식

HRID 570924 반응식
[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]

참가 물질

4

반응물 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

생성물 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)-one수율 73%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2a86ef82ff9543bd876d44a759202d65
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024018B2

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