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 570924Notes

Reaction equation

HRID 570924 reaction equation
[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]

Participants

4

Reactant 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

Product 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)-oneYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-2a86ef82ff9543bd876d44a759202d65
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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