Triethylamine → HCID 53706284, compound

HRID 343353Notes

Reaction equation

HRID 343353 reaction equation
Cl.CN(C)CCCN=C=NCC.[NH:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22]([OH:24])=O)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1.Cl.[C:26]1(/[CH:32]=[CH:33]/[C:34]2[CH2:35][CH2:36][NH:37][CH2:38][CH:39]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.O>[NH:13]1[C:21]2[C:16](=[CH:17][C:18]([C:22]([N:37]3[CH2:36][CH:35]=[C:34]([CH:33]=[CH:32][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:39][CH2:38]3)=[O:24])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 742801H-Indole-5-Carboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67582496HCID 67582496, compound

Product 1

HCID 53706284HCID 53706284, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.77 g, 4.02 mmol) was added to a mixture of indole-5-carboxylic acid (0.45 g, 2.79 mmol), (E)-4-(2-phenylethenyl)-1,2,3,6-tetrahydropyridine hydrochloride (0.59 g, 2.66 mmol), 1-hydroxybenzotriazole hydrate (0.56 g, 3.3 mmol) and triethylamine (1.1 ml, 7.9 mmol) in dimethylformamide (20 ml). The reaction mixture was stirred at room temperature, under nitrogen, overnight then poured into water (200 ml) and extracted with ethyl acetate (2×100 ml). The extracts were washed with 1M hydrochloric acid (2×100 ml), saturated brine (100 ml), combined and dried (MgSO4). The residue after evaporation of the solvent was purified by flash chromatography, eluting with 2:1, 3:1 then 4:1 ethyl acetate/petrol (60°-80°), to afford the title compound as an off-white solid (0.55 g, 63%); δH (CDCl3) 2.50 (2H, br s, tetrahydropyridinyl CH2), 3.76 (2H, v br s, tetrahydropyridinyl CH2), 4.31 (2H, v br s, tetrahydropyridinyl CH2), 5.84 (1H, v br s, tetrahydropyridinyl CH), 6.51 (1H, d, J 16.2 Hz, CH=CHPh), 6.60 (1H, br s, 3'-H), 6.81 (1H, d, J 16.2 Hz, CH=CHPh), 7.20-7.42 (9H, m, ArH), 7.42 (1H, s, ArH), and 8.46 (1H, br s, NH).

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. washThe extracts were washed with 1M hydrochloric acid (2×100 ml), saturated brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. customThe residue after evaporation of the solvent
  5. customwas purified by flash chromatography
  6. washeluting with 2:1, 3:1

Sources & evidence

ORD record
ord-16aed9d2d5ce480dba38abd467c270e5
Source dataset
uspto-grants-1999_01
Patent number
US05861407

Reaction notes

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