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

HRID 570973

반응식

HRID 570973 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-2ba70a7f72674459abcd25cdb7b935b0
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024018B2

연결된 노트

불러오는 중…