Triethylamine → HCID 22141259, compound

HRID 428980

Reaction equation

HRID 428980 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:9][C:4]=2[O:3][CH2:2]1.O.O[N:17]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[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(N(CC)CC)C>CN(C)C=O>[NH3:17].[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][C:12]([N:42]3[CH2:43][CH:44]4[CH:40]([C:39]4([C:45]4[CH:46]=[C:47]([NH:51][S:52]([CH3:55])(=[O:54])=[O:53])[CH:48]=[CH:49][CH:50]=4)[CH3:38])[CH2:41]3)=[O:14])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 648103-(Benzodioxol-5-yl)propionic 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 22141259HCID 22141259, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(1,3-benzodioxol-5-yl)propanoic acid (120 mg, 0.62 mmol) in N,N-dimethylformamide (13 ml) was added 1-hydroxybenzotriazole monohydrate (100 mg, 0.66 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (170 mg, 0.88 mmol). After stirring at room temperature for 5 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, 200 mg, 0.66 mmol) and triethylamine (133 mg, 1.32 mmol). The reaction mixture was stirred at room temperature for 72 h before concentrating in vacuo. Water (10 ml) was added and the reaction mixture was extracted with ethyl acetate (2×15 ml). The combined organic extracts were washed with water (10 ml) and saturated brine (10 nml), dried (Na2SO4), filtered and concentrated in vacuo to give a light brown oil. The residue was purified by chromatography using a Sep-Pak™ cartridge packed with silica gel (10 g) eluting with dichloromethane:ethanol: 0.88 ammonia (300:8:1) to afford the title compound as a white foam (107 mg, 38%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 72 h
  2. concentrationbefore concentrating in vacuo
  3. additionWater (10 ml) was added
  4. extractionthe reaction mixture was extracted with ethyl acetate (2×15 ml)
  5. washThe combined organic extracts were washed with water (10 ml) and saturated brine (10 nml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a light brown oil
  10. customThe residue was purified by chromatography
  11. washeluting with dichloromethane

Sources & evidence

ORD record
ord-ac32867ce25c4c88b3ee395b803523df
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Linked notes

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