Methyl N-(triethylammoniosulfonyl)carbamate → HCID 66831858, compound

HRID 570938Notes

Reaction equation

HRID 570938 reaction equation
[C:1]([NH:9][NH:10][C:11]([C:13]1[N:14]=[CH:15][N:16]2[C:21](=[O:22])[N:20]([CH2:23][S:24][CH3:25])[N:19]=[N:18][C:17]=12)=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COC(=NS([N+](CC)(CC)CC)(=O)=O)[O-]>C1COCC1>[CH3:25][S:24][CH2:23][N:20]1[C:21](=[O:22])[N:16]2[CH:15]=[N:14][C:13]([C:11]3[O:12][C:1]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[N:9][N:10]=3)=[C:17]2[N:18]=[N:19]1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 66831694HCID 66831694, compound

Product 1

HCID 66831858HCID 66831858, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N′-benzoyl-3-(methylthiomethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbohydrazide (0.47 mmol, 170 mg, 1 eq.) and 1-methoxy-N-triethylammoniosulfonyl-methanimidate (Burgess Reagent) (1.61 mmol, 383 mg, 3.4 eq.) were dissolved in THF (8 mL). Microwave energy was applied to the solution for 5 minutes, keeping reaction temperature at 60° C. The reaction mixture was poured into ice/water and the formed solid was filtered and washed with water, acetonitrile and ether, and dried under vacuum to give the title compound. Yield 71%. δH (DMSO-d6) 8.90 (1H, bs), 7.92 (2H, bs), 7.49 (3H, bs), 5.29 (2H, bs), 2.09 (3H, bs).

Workup

  1. customreaction temperature at 60° C
  2. filtrationthe formed solid was filtered
  3. washwashed with water, acetonitrile and ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-d1d08fdb179943d1847763fcaa1502ae
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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