Triethylamine → 8-(2,4'-Bithiazol-2'-yl)-3-(prop-2-ynyl)imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-one

HRID 570925Notes

Reaction equation

HRID 570925 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][N:25]=1)=O.C(N(CC)CC)C>CC#N>[S:22]1[CH:23]=[CH:24][N:25]=[C:21]1[C:19]1[N:15]=[C:14]([C:11]2[N:12]=[CH:13][N:3]3[C:2](=[O:1])[N:7]([CH2:8][C:9]#[CH:10])[N:6]=[N:5][C:4]=23)[S:16][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27952122-Bromo-1-(1,3-thiazol-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 498706418-(2,4'-Bithiazol-2'-yl)-3-(prop-2-ynyl)imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-oneYield 38%

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-(1,3-thiazol-2-yl)ethanone (0.43 mmol) were stirred in MeCN (2 mL) overnight at room temperature. The reaction mixture containing a newly formed precipitate was then treated with sufficient triethylamine to solubilise before evaporating to dryness and purifying by column chromatography, eluting with 10% MeCN/DCM, to give the title compound. Yield 38%. δH (DMSO-d6) 9.00 (1H, s) 8.44 (1H, s), 7.97 (1H, d, J=3.2), 7.85 (1H, d, J=2.8), 5.16 (2H, d, J=2.4), 3.55 (1H, t, J=2.4).

Workup

  1. additionThe reaction mixture containing a newly formed precipitate
  2. custombefore evaporating to dryness
  3. custompurifying by column chromatography
  4. washeluting with 10% MeCN/DCM

Sources & evidence

ORD record
ord-8779379a894d4816bb440255bd9864f7
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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