Triethylamine → HCID 57291699, compound

HRID 890787Notes

Reaction equation

HRID 890787 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[CH:5]=1.C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][CH2:12][N:13]([CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[S:33]([CH3:32])(=[O:35])=[O:34])[CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57003689HCID 57003689, compound

Product 1

HCID 57291699HCID 57291699, compoundYield 115.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(3-{[3-(3-chloro-phenyl)-propyl]-amino}-propyl)-benzoic acid methyl ester (50.3 mg, 0.145 mmol) and triethylamine (32.4 mg, 0.32 mmol) in CH2Cl2 (10 mL) was added methanesulfonyl chloride (18.3 mg, 0.16 mmol) at 0° C. The reaction mixture was stirred for 24 h at room temperature and was diluted with CH2Cl2. The organic solution was washed consecutively with aqueous HCl (5.5%, 1×), H2O (1×), NaHCO3 (1×) and brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated to afford the title product of Step A as an oil (71 mg). MS 424 (M+1).

Workup

  1. washThe organic solution was washed consecutively with aqueous HCl (5.5%, 1×), H2O (1×), NaHCO3 (1×) and brine (1×)
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9323b228582344e5b1434f94527936cd
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

Loading…