Sodium Bicarbonate → HCID 22141136, compound

HRID 1826501Notes

Reaction equation

HRID 1826501 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[CH:7]/[C:8]([OH:10])=O.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:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH2:39]2

Participants

7

Reactant 5

HCID 516892Sodium BicarbonateHCID 7359813-(2-Thienyl)acrylic 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 22141136HCID 22141136, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-3-(2-thienyl)-2-propenoic acid (200 mg, 1.08 mmol) 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 (15 ml) and ethyl acetate (20 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 (337 mg, 77%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 7 d
  2. concentrationconcentrated in vacuo
  3. customAttempted partition between water (15 ml) and ethyl acetate (20 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-aefb475a246349aaad2dc2c9582c865d
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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