Triethylamine → 2-(3-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazin-8-yl)-N-(prop-2-ynyl)thiazole-4-carboxamide

HRID 570928Notes

Reaction equation

HRID 570928 reaction equation
[NH:1]=[C:2]([C:10]1[N:11]=[CH:12][N:13]2[C:18](=[O:19])[N:17]([CH3:20])[N:16]=[N:15][C:14]=12)[S:3][CH2:4][C:5](=O)[C:6]([OH:8])=O.ClC(OCC(C)C)=O.C(N(CC)CC)C.[CH2:36]([NH2:39])[C:37]#[CH:38]>C1COCC1>[CH3:20][N:17]1[C:18](=[O:19])[N:13]2[CH:12]=[N:11][C:10]([C:2]3[S:3][CH:4]=[C:5]([C:6]([NH:39][CH2:36][C:37]#[CH:38])=[O:8])[N:1]=3)=[C:14]2[N:15]=[N:16]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 239041PropargylamineHCID 668316143-(Imino(3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazin-8-yl)methylthio)-2-oxopropanoic acid

Product 1

HCID 498699872-(3-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazin-8-yl)-N-(prop-2-ynyl)thiazole-4-carboxamideYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(imino(3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazin-8-yl)methylthio)-2-oxopropanoic acid (0.65 g; 2.2 mmol) in dry THF (30 mL) under nitrogen was added isobutyl chloroformate (0.60 mL; 4.4 mmol), followed by triethylamine (0.62 mL; 4.4 mmol). The mixture was stirred for 1 hour, and then propargylamine (0.28 mL; 4.4 mmol) was added, and stirring continued for a further 3 hours. The precipitate was washed with water (5×15 mL) and diethyl ether (2×15 mL) to yield the title compound as a pale yellow solid (0.250 g; 36%). δH (DMSO-d6) 3.13 (1H, m), 3.89 (3H, s), 4.10 (2H, m), 8.47 (1H, s), 8.68 (1H, t, J=5.9), 8.95 (1H, s).

Workup

  1. stirringstirring
  2. waitcontinued for a further 3 hours
  3. washThe precipitate was washed with water (5×15 mL) and diethyl ether (2×15 mL)

Sources & evidence

ORD record
ord-85fdd20922514092af927194230542a8
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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