Sodium Bicarbonate → HCID 22141292, compound

HRID 428993Notes

Reaction equation

HRID 428993 reaction equation
O.O[N:3]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1/[CH:30]=[CH:31]/[C:32]([OH:34])=O.[CH3:35][C:36]1([C:42]2[CH:43]=[C:44]([NH:48][S:49]([CH3:52])(=[O:51])=[O:50])[CH:45]=[CH:46][CH:47]=2)[CH:41]2[CH:37]1[CH2:38][NH:39][CH2:40]2.C(=O)([O-])O.[Na+]>CN(C)C=O.ClCCl.O>[NH3:3].[CH3:35][C:36]1([C:42]2[CH:43]=[C:44]([NH:48][S:49]([CH3:52])(=[O:51])=[O:50])[CH:45]=[CH:46][CH:47]=2)[CH:41]2[CH:37]1[CH2:38][N:39]([C:32](=[O:34])/[CH:31]=[CH:30]/[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=1)[CH2:40]2

Participants

10

Reactant 5

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 53566263-(Pyridin-2-yl)prop-2-enoic acidHCID 22141143N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl)methanesulfonamide

Product 2

HCID 222AmmoniaHCID 22141292HCID 22141292, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-hydroxybenzotriazole monohydrate (224 mg, 1.46 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (306 mg, 1.60 mmol) in N,N-dimethylformamide (10 ml) was added to (E)-3-(2-pyridinyl)-2-propenoic acid (197 mg, 1.32 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, 404 mg, 1.32 mmol) and sodium hydrogen carbonate (220 mg, 2.64 mmol). The reaction mixture was stirred at room temperature for overnight and then water (20 ml) and dichloromethane (10 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 377 mg of a crude dark brown oil. 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 a white solid (172 mg, 33%).

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 377 mg of a crude dark brown oil
  8. customThis was purified by chromatography
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-489145e5aeec47859946c658c1ac0bc1
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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