O-Benzylhydroxylamine → N-(Benzyloxy)-3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

HRID 570973

反応式

HRID 570973 の反応式
[CH2:1]([O:8][NH2:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][N:11]1[C:16](=[O:17])[N:15]2[CH:18]=[N:19][C:20]([C:21](Cl)=[O:22])=[C:14]2[N:13]=[N:12]1>C1COCC1.O>[CH2:1]([O:8][NH:9][C:21]([C:20]1[N:19]=[CH:18][N:15]2[C:16](=[O:17])[N:11]([CH3:10])[N:12]=[N:13][C:14]=12)=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 102313O-BenzylhydroxylamineHCID 110202383-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbonyl chloride

生成物 1

HCID 49869276N-(Benzyloxy)-3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide収率 63%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

O-benzylhydroxylamine (195 μL, 1.68 mmol, 2 eq.) was added to a solution of crude 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbonyl chloride (200 mg, 0.84 mmol; see Arrowsmith et al., J. Med. Chem., 2002, Vol. 45, No. 25, p. 5458) in THF (6 mL) and a precipitate formed instantly. The resulting suspension was stirred for 1 hour and 30 minutes and was then poured into ice. The suspension was diluted with water and the precipitate was filtered and washed successively with water, ethyl acetate and diethyl ether to give 158 mg of the pure title compound as an off-white solid (63% yield). δH (DMSO-d6): 11.9 (1H, s), 8.85 (1H, s), 7.42-7.50 (2H, m), 7.36-7.42 (3H, m), 4.96 (2H, s), 3.88 (3H, s).

後処理

  1. additionwas then poured into ice
  2. filtrationthe precipitate was filtered
  3. washwashed successively with water, ethyl acetate and diethyl ether

出典と根拠

ORDレコード
ord-2ba70a7f72674459abcd25cdb7b935b0
出典データセット
uspto-grants-2015_05
特許番号
US09024018B2

関連ノート

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