Hydrochloric Acid → HCID 178428599, 화합물

HRID 69801노트

반응식

HRID 69801 반응식
[OH:1][N:2]=[C:3]([C:5]1[C:9]([NH:10][CH2:11][CH2:12][NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[N:8][O:7][N:6]=1)[NH2:4].Cl.N([O-])=O.[Na+].[F:23][C:24]1[CH:30]=[CH:29][C:27](N)=[CH:26][C:25]=1[CH3:31]>O1CCOCC1.O.C(O)C>[F:23][C:24]1[CH:30]=[CH:29][C:27]([NH:4][C:3]([C:5]2[C:9]([NH:10][CH2:11][CH2:12][NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[N:8][O:7][N:6]=2)=[N:2][OH:1])=[CH:26][C:25]=1[CH3:31]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 679814-Fluoro-m-toluidine2회HCID 23668193Sodium NitriteHCID 136330166N-hydroxy-4-({2-[(methylsulfonyl)amino]ethyl}amino)-1,2,5-oxadiazole-3-carboximidamide

생성물 1

HCID 178428599HCID 178428599, 화합물수율 35.1%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
0 °C

실험 절차

N′-Hydroxy-4-({2-[(methylsulfonyl)amino]ethyl}amino)-1,2,5-oxadiazole-3-carboximidamide (35 mg, 0.13 mmol) was stirred in 1,4-dioxane (2 mL) and 6 N hydrogen chloride solution (4 mL) was added. The solution was cooled to 0° C. and a solution of sodium nitrite (11 mg, 0.16 mmol) in water (3 mL) was slowly added. The mixture was stirred for 1 hour at 0° C. and evaporated. Dry 1,4-dioxane (2 mL) was added and the mixture evaporated two more times. A solution of 4-fluoro-3-methylaniline [Aldrich, product #559415] (25 mg, 0.20 mmol) in ethanol (2 mL) was added and the mixture was stirred for 1 hour. Purification by preparative LCMS (pH 2) gave the desired compound (17 mg, 27%). LCMS calculated for C13H18FN6O4S (M+H)+: m/z=373.1. 1H NMR (400 MHz, DMSO-d6): δ 11.25 (s, 1H), 8.61 (s, 1H), 7.18 (m, 1H), 6.91 (m, 1H), 6.72 (m, 1H), 6.58 (m, 1H), 6.24 (s, 1H), 3.32 (m, 2H), 3.11 (m, 2H), 2.89 (s, 3H), 2.05 (s, 3H).

후처리

  1. customevaporated
  2. additionDry 1,4-dioxane (2 mL) was added
  3. customthe mixture evaporated two more times
  4. stirringthe mixture was stirred for 1 hour
  5. customPurification by preparative LCMS (pH 2)

출처 및 근거

ORD 기록
ord-b20e39fa777441f39370faaa47721b75
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822511B2

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