Sodium Bicarbonate → HCID 22141297, compound

HRID 428989Notes

Reaction equation

HRID 428989 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1/[CH:7]=[CH:8]/[C:9]([OH:11])=O.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[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>[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:9](=[O:11])/[CH:8]=[CH:7]/[C:3]1[S:4][CH:5]=[CH:6][C:2]=1[CH3:1])[CH2:40]2

Participants

7

Reactant 5

HCID 516892Sodium BicarbonateHCID 14852383-(3-methylthiophen-2-yl)prop-2-enoic 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 22141297HCID 22141297, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-3-(3-methyl-2-thienyl)-2-propenoic acid (200 mg, 1.00 mmol) in N,N-dimethylformamide (20 ml) was added 1-hydroxybenzotriazole monohydrate (212 mg, 1.39 mmol) and 1-(3-dimethylarninopropyl)-3-ethylcarbodiimide hydrochloride (352 mg, 1.84 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, 414 mg, 1.36 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 (280 mg, 67%).

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-da0204338e804da2b9cc6d59d64067fa
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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