Triethylamine → HCID 22141167, compound

HRID 428975Notes

Reaction equation

HRID 428975 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10]([OH:12])=O.O.O[N:15]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:36][C:37]1([C:43]2[CH:44]=[C:45]([NH:49][S:50]([CH3:53])(=[O:52])=[O:51])[CH:46]=[CH:47][CH:48]=2)[CH:42]2[CH:38]1[CH2:39][NH:40][CH2:41]2.C(N(CC)CC)C>>[NH3:15].[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][CH:2]1[C:10]([N:40]1[CH2:41][CH:42]2[CH:38]([C:37]2([C:43]2[CH:44]=[C:45]([NH:49][S:50]([CH3:53])(=[O:52])=[O:51])[CH:46]=[CH:47][CH:48]=2)[CH3:36])[CH2:39]1)=[O:12]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 5757772-Indancarboxylic 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 22141167HCID 22141167, compoundYield 46%

Procedure

To a solution of 2-indane carboxylic acid (E. D. Bergmann and E. Hoffrnann, J. Org. Chem., 1961, 26, 3555, 100 mg, 0.62 mmol) in N,N-imethylformamide (13 ml) was added 1-hydroxybenzotriazole monohydrate (100 mg, 0.66 mmol) and 1-(3dimethylaminopropyl)-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 ml), 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 (117 mg, 43%).

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 ml)
  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-6c686147629042b29923d0d48bebc551
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

Loading…