Diisopropylethylamine → HCID 69321849, compound

HRID 749255Notes

Reaction equation

HRID 749255 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9](CS(N)(=O)=O)[CH:10]=1)[OH:4].C(N(C(C)C)CC)(C)C.Br[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]1[CH:39]=[C:40]([S:44]([NH2:47])(=[O:46])=[O:45])[CH:41]=[CH:42][CH:43]=1>CN(C)C=O>[CH:8]([OH:16])=[O:33].[OH:4][C@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:47][S:44]([CH3:40])(=[O:46])=[O:45])[CH:10]=1)[CH2:2][NH:1][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]1[CH:39]=[C:40]([S:44]([NH2:47])(=[O:46])=[O:45])[CH:41]=[CH:42][CH:43]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 21895438Benzenesulfonamide, 3-[4-[(6-bromohexyl)oxy]butyl]-HCID 23553464HCID 23553464, compound

Product 1

HCID 69321849HCID 69321849, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1-{5-[(1R)-2-amino-1-hydroxyethyl]-2-hydroxyphenyl}methanesulfonamide (65 mg), diisopropylethylamine (0.06 ml) and 3-{4-[(6-bromohexyl)oxy]butyl}benzenesulfonamide (86 mg) in N,N-dimethylformamide (1 ml) under nitrogen was heated to 50° for 48 h. The mixture was cooled to 20°, the solvent evaporated in vacuo and the residue purified by mass-directed autopreparative HPLC to give the title compound (12 mg). LCMS RT=2.31 min ES+ve 558 (MH)+.

Workup

  1. temperatureThe mixture was cooled to 20°
  2. customthe solvent evaporated in vacuo
  3. customthe residue purified by mass-directed autopreparative HPLC

Sources & evidence

ORD record
ord-edb9db21d9084b90bdd1903849d155af
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Reaction notes

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