(Bis(2-methoxyethyl)amino)sulfur trifluoride → HCID 71598577, compound

HRID 533128Notes

Reaction equation

HRID 533128 reaction equation
COCCN(S(F)(F)[F:11])CCOC.[CH3:14][S:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:25]=[CH:26][C:27]3[O:31][CH:30]([CH:32]4[CH2:37][CH2:36][N:35]([CH2:38][C:39]([CH3:42])(O)[CH3:40])[CH2:34][CH2:33]4)[CH2:29][C:28]=3[CH:43]=2)=[CH:20][CH:19]=1)(=[O:17])=[O:16]>C1(C)C=CC=CC=1.ClCCl.CO>[F:11][C:39]([CH3:42])([CH3:40])[CH2:38][N:35]1[CH2:36][CH2:37][CH:32]([CH:30]2[CH2:29][C:28]3[CH:43]=[C:24]([C:21]4[CH:22]=[CH:23][C:18]([S:15]([CH3:14])(=[O:17])=[O:16])=[CH:19][CH:20]=4)[CH:25]=[CH:26][C:27]=3[O:31]2)[CH2:33][CH2:34]1

Participants

6

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 86686882HCID 86686882, compound

Product 1

HCID 71598577HCID 71598577, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of [bis(2-methoxyethyl)amino]sulfur trifluoride in toluene (50%; 162 μL) is added to an ice-cooled solution of 1-{4-[5-(4-methanesulfonyl-phenyl)-2,3-dihydro-benzofuran-2-yl]-piperidin-1-yl}-2-methyl-propan-2-ol (100 mg) in dichloromethane (2 mL) and the resulting mixture is stirred for 16 h. The reaction mixture is diluted with methanol and concentrated in vacuo. The residue is purified by HPLC to give the title compound. LC (method 1): tR=1.17 min; Mass spectrum (ESI+): m/z=432 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-220f9b32e6fc49c986d61810a61ceedd
Source dataset
uspto-grants-2014_10
Patent number
US08853239B2

Reaction notes

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