Dimethylformamide → 3-Methyl-4-oxo-N-(2-oxo-2-phenylethyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

HRID 570931Notes

Reaction equation

HRID 570931 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[N:6]2[CH:9]=[N:10][C:11]([C:12](Cl)=[O:13])=[C:5]2[N:4]=[N:3]1.Cl.[NH2:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19].CN(C=O)C>N1C=CC=CC=1>[CH3:1][N:2]1[C:7](=[O:8])[N:6]2[CH:9]=[N:10][C:11]([C:12]([NH:16][CH2:17][C:18](=[O:19])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:13])=[C:5]2[N:4]=[N:3]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)HCID 110202383-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbonyl chloride

Product 1

HCID 668317663-Methyl-4-oxo-N-(2-oxo-2-phenylethyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbonyl chloride (0.620 g; 2.90 mmol) and 2-aminoacetophenone hydrochloride (0.500 g; 2.90 mmol) was added DMF (6 mL) and pyridine (1.2 mL). The reaction mixture was stirred for 16 hours at room temperature, and then poured onto water. The precipitate was filtered, washed with water, and dried in the vacuum oven, and used without further purification. δH (DMSO-d6) 8.89 (1H, s), 8.68 (1H, t, J=5.6), 8.06 (2H, dd, J=8.3, 1.2), (1H, tt, J=7.4, 1.8), 7.58 (2H, m), 4.86 (1H, d, J=5.6), 3.89 (3H, s).

Workup

  1. additionpoured onto water
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried in the vacuum oven
  5. customused without further purification

Sources & evidence

ORD record
ord-633a4f5d40d34df587be9b2509763842
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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