Sodium Bicarbonate → HCID 22141163, compound

HRID 1826510Notes

Reaction equation

HRID 1826510 reaction equation
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]

Participants

10

Reactant 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

Product 2

HCID 222AmmoniaHCID 22141163HCID 22141163, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-3067aac148ed4103bd702a5dfee9043b
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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