Triethylamine → HCID 49869277, compound

HRID 570972Notes

Reaction equation

HRID 570972 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]([OH:16])=O)[N:12]=[CH:13][N:3]12.C(N(CC)CC)C.[CH2:24]([O:31][NH2:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1.CN(C=O)C>[CH2:24]([O:31][NH:32][C:14]([C:11]1[N:12]=[CH:13][N:3]2[C:2](=[O:1])[N:7]([CH2:8][C:9]#[CH:10])[N:6]=[N:5][C:4]=12)=[O:16])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 102313O-BenzylhydroxylamineHCID 86663797HCID 86663797, compound

Product 1

HCID 49869277HCID 49869277, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-oxo-3-(prop-2-ynyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid (0.46 mmol, 100 mg, 1 eq.), O-Benzotriazole-N,N,N′,N′-tetramethyl-uronium-hexafluoro-phosphate (HBTU) (0.55 mmol, 208 mg, 1.2 eq.) and triethylamine (0.55 mmol, 77 μL, 1.2 eq.) were dissolved in THF (30 mL) and DMF (1 mL). The mixture was stirred at room temperature for 1 hour before adding O-benzylhydroxylamine (0.55 mmol, 68 mg, 1.2 eq.) in one portion. After 24 hours of room temperature stirring, the volume of the solution was reduced to 5 mL and poured into ice/water. The formed solid was filtered and washed with water, ethyl acetate and ether, and dried under vacuum. Yield: 72%. δH (DMSO-d6) 11.93 (1H, bs), 8.89 (1H, s), 7.48 (2H, m), 7.40 (3H, m), 5.15 (2H, d, J: 1.84), 4.97 (2H, s), 3.53 (1H, bs).

Workup

  1. stirringAfter 24 hours of room temperature stirring
  2. filtrationThe formed solid was filtered
  3. washwashed with water, ethyl acetate and ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-bc3061ec4c594a2cbc45cb4d14afb154
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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