Sodium Bicarbonate → N-(3-{6-methyl-3-[(E)-3-(3-thienyl)-2-propenoyl]-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide

HRID 428987Notes

Reaction equation

HRID 428987 reaction equation
[S:1]1[CH:5]=[CH:4][C:3](/[CH:6]=[CH:7]/[C:8]([OH:10])=O)=[CH:2]1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:34][C:35]1([C:41]2[CH:42]=[C:43]([NH:47][S:48]([CH3:51])(=[O:50])=[O:49])[CH:44]=[CH:45][CH:46]=2)[CH:40]2[CH:36]1[CH2:37][NH:38][CH2:39]2.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:34][C:35]1([C:41]2[CH:42]=[C:43]([NH:47][S:48]([CH3:51])(=[O:50])=[O:49])[CH:44]=[CH:45][CH:46]=2)[CH:40]2[CH:36]1[CH2:37][N:38]([C:8](=[O:10])/[CH:7]=[CH:6]/[C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)[CH2:39]2

Participants

7

Reactant 5

HCID 516892Sodium BicarbonateHCID 735793(2E)-3-(3-Thienyl)-2-propenoic 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 1

HCID 22141215N-(3-{6-methyl-3-[(E)-3-(3-thienyl)-2-propenoyl]-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamideYield 82.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-3-(3-thienyl)-2-propenoic acid (200 mg, 1.08 nmmol) in N,N-dimethylformamide (20 ml) was added 1-hydroxybenzotriazole monohydrate (225 mg, 1.47 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (328 mg, 1.71 mmol). After stirring at room temperature for 10 min, the mixture was treated with the hydrochloride salt of N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl]methanesulfonamide (Preparation 53, 449 mg, 1.48 mmol) and sodium hydrogen carbonate (225 mg, 2.68 mmol). The reaction mixture was stirred at room temperature for 7 d and then concentrated in vacuo. Attempted partition between water (10 ml) and ethyl acetate (15 ml) produced a buff solid which was collected by filtration. Sonication for 5 min at room temperature in dichloromethane (5 ml) followed by filtration afforded the title compound as an off-white solid (430 mg, 72%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 7 d
  2. concentrationconcentrated in vacuo
  3. customAttempted partition between water (10 ml) and ethyl acetate (15 ml)
  4. customproduced a buff solid which
  5. filtrationwas collected by filtration
  6. customSonication for 5 min at room temperature in dichloromethane (5 ml)
  7. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-cee8ddda60904837bffab8e7e935c898
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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