Triethylamine → HCID 9891973, compound

HRID 1600164Notes

Reaction equation

HRID 1600164 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:19]=[C:18]2[CH2:30][C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1.C(N(CC)CC)C>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][CH2:13][CH2:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:19]=[C:18]3[CH2:30][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 18926565HCID 18926565, compound

Product 1

HCID 9891973HCID 9891973, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Fluorobenzenesulphonyl chloride (0.346 g) was added portionwise to a stirred solution of methyl 5-(2-aminoethyl)-3-(3-pyridylmethyl)-1H-indole1-propanoate (0.50 g) and triethylamine (0.33 g) in dichloromethane (5 ml) at room temperature. The mixture was stirred for 30 minutes and then washed with water and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel using dichloromethane/methanol (50:1) as eluant. The product fractions were combined and evaporated to give the title compound as a gum (0.59 g).

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customThe solvent was evaporated
  4. customthe residue was chromatographed on silica gel
  5. customevaporated

Sources & evidence

ORD record
ord-75118f4cfd5a42be90694b0bcc98a719
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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