Dimethylamine → HCID 59513535, compound

HRID 1159861Notes

Reaction equation

HRID 1159861 reaction equation
I[CH:2]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH3:3].[NH:22]([CH3:24])[CH3:23]>C(Cl)Cl.CCO>[CH3:23][N:22]([CH3:24])[CH:2]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH3:3]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 68717446HCID 68717446, compound2×

Product 1

HCID 59513535HCID 59513535, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(1-iodoethyl)-1-(phenylsulfonyl)-1H-indole (40 mg, 97.3 μmol; Intermediate 99) in CH2Cl2 (1.5 mL) was treated with Me2NH (174 μL of a 5.6 M solution in EtOH, 973 μmol) at rt for 1 h. The reaction mixture was concentrated in vacuo, the obtained residue taken up with MeOH/THF and purified by prep. HPLC (System B, 30-60% MeCN, 50 mM NH4HCO3) to yield the title compound as a white, waxy solid (10.6 mg, 11% over two steps). MS (ESI+) for C18H20N2O2S m/z 329 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by prep

Sources & evidence

ORD record
ord-1b40c37a482d4659b6af282350c89304
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

Loading…