Triethylamine → HCID 10671584, compound

HRID 725023Notes

Reaction equation

HRID 725023 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:7]=[C:8]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:9]=1.[CH:24]1([S:30](Cl)(=[O:32])=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[CH2:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH:24]1[S:30]([NH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:7]=[C:8]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:9]=1)(=[O:32])=[O:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 237554Cyclohexanesulfonyl chlorideHCID 10733906HCID 10733906, compound

Product 1

HCID 10671584HCID 10671584, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 3-[3-(2-aminoethyl)-5-(3-pyridylmethyl)phenyl]propanoate (Preparation 47; 0.60 g), cyclohexylsulphonyl chloride (0.526 g), triethylamine (0.194 g) and 4-dimethylaminopyridine (0.352 g) in dichloromethane (6 ml) was stirred at room temperature for 3 hours and then washed with water and dried (MgSO4). Evaporation under vacuum of the solvent gave a gum which was chromatographed on silica gel. Elution with dichloromethane, followed by a dichloromethane:methanol (97:3) mixture gave the title compound as a gum (401 mg); Rf 0.70 (SS 2); δ (CDCl3): 1.10-1.25(2H,m), 1.21(3H,t,J=7.1 Hz), 1.37-1.50(2H,m), 1.65-1.70(2H,m), 1.83-1.86(2H,m), 2.05-2.09(2H,m), 2.57(2H,t,J=7.7 Hz), 2.79(2H,t,J=6.9 Hz), 2.88 (2H,t,J=7.7 Hz), 3.30-3.37(2H,m), 3.91(2H,s), 3.99-4.02 (1H,m), 4.10(2H,q,J=7.1 Hz), 6.86(1H,s), 6.89(1H,s), 6.91(1H,s), 7.21-7.23(1H,m), 7.44(1H,d,J=7.9 Hz), 8.45-8.47(2H,m).

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customEvaporation under vacuum of the solvent
  4. customgave a gum which
  5. customwas chromatographed on silica gel
  6. washElution with dichloromethane

Sources & evidence

ORD record
ord-165f3803b71c448b873c04f952ea5f39
Source dataset
uspto-grants-1998_01
Patent number
US05705523

Reaction notes

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