Sodium Bicarbonate → HCID 22141163, 화합물

HRID 1826510노트

반응식

HRID 1826510 반응식
O.O[N:3]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[S:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N:26]=[C:25]1[CH2:33][CH2:34][C:35]([OH:37])=O.[CH3:38][C:39]1([C:45]2[CH:46]=[C:47]([NH:51][S:52]([CH3:55])(=[O:54])=[O:53])[CH:48]=[CH:49][CH:50]=2)[CH:44]2[CH:40]1[CH2:41][NH:42][CH2:43]2.C(=O)([O-])O.[Na+]>CN(C)C=O.ClCCl.O>[NH3:3].[S:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N:26]=[C:25]1[CH2:33][CH2:34][C:35]([N:42]1[CH2:43][CH:44]2[CH:40]([C:39]2([C:45]2[CH:46]=[C:47]([NH:51][S:52]([CH3:55])(=[O:54])=[O:53])[CH:48]=[CH:49][CH:50]=2)[CH3:38])[CH2:41]1)=[O:37]

참가 물질

10

반응물 5

HCID 516892Sodium BicarbonateHCID 7709763-(1,3-Benzothiazol-2-yl)propanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22141143N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl)methanesulfonamide

생성물 2

HCID 222AmmoniaHCID 22141163HCID 22141163, 화합물수율 76%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

A solution of 1-hydroxybenzotriazole monohydrate (112 mg, 0.73 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (153 mg, 0.80 mmol) in N,N-dimethylformamide (5 ml) was added to 3-(1,3-benzothiazol-2-yl)propanoic acid (P. Baudet and C. Otten, Helv. Chim. Acta, 1970, 53, 1683; 137 mg, 0.66 mmol). After stirring at room temperature for 15 min, the mixture was added to the hydrochloride salt of N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl]methanesulfonamide (Preparation 53, 202 mg, 0.66 mmol) and sodium hydrogen carbonate (110 mg, 1.32 mmol). The reaction mixture was stirred at room temperature for overnight and then water (10 ml) and dichloromethane (5 ml) were added. The biphasic mixture was separated by filtering through a Whatman Microfiltration Device Filter Tube, and the resulting organic extract was concentrated using a stream of nitrogen to afford 326 mg of a crude dark green solid. This was purified by chromatography using a Biotage Flash 40S™ cartridge packed with silica gel (40 g) eluting with dichloromethane:ethanol:0.880 ammonia (100:2:1) to afford the title compound as an off-white solid (228 mg, 76%).

후처리

  1. stirringThe reaction mixture was stirred at room temperature for overnight
  2. customThe biphasic mixture was separated
  3. filtrationby filtering through a Whatman Microfiltration Device
  4. filtrationFilter Tube
  5. extractionthe resulting organic extract
  6. concentrationwas concentrated
  7. customto afford 326 mg of a crude dark green solid
  8. customThis was purified by chromatography
  9. washeluting with dichloromethane

출처 및 근거

ORD 기록
ord-3067aac148ed4103bd702a5dfee9043b
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07049444B2

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