Diisopropylethylamine → HCID 59447433, compound

HRID 1873846Notes

Reaction equation

HRID 1873846 reaction equation
[CH:1]1([O:4][C:5]2[CH:13]=[C:12]([S:14][CH3:15])[C:8]([C:9]([OH:11])=O)=[C:7]([S:16][CH3:17])[CH:6]=2)[CH2:3][CH2:2]1.[CH3:18][C:19]([CH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)([S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1)(=[O:23])=[O:22])[CH3:20].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(OCC)(=O)C.CN(C)C=O>[CH:1]1([O:4][C:5]2[CH:6]=[C:7]([S:16][CH3:17])[C:8]([C:9]([N:37]3[CH2:38][CH2:39][CH:34]([C:19]([CH3:20])([S:21]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:31])[F:32])[CH:25]=4)(=[O:22])=[O:23])[CH3:18])[CH2:35][CH2:36]3)=[O:11])=[C:12]([S:14][CH3:15])[CH:13]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59447296HCID 59447296, compoundHCID 594474094-(1-Methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidine

Product 1

HCID 59447433HCID 59447433, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 16 ml vial was added 4-(cyclopropyloxy)-2,6-bis(methylthio)benzoic acid (375 mg, 1.39 mmol), 4-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperdine (465 mg, 1.39 mmol), Bop reagent (675 mg, 1.53 mmol), diisopropylethyl amine (1.21 ml, 6.93 mmol) and 4 ml dimethylformamide. The resulting solution was stirred at room temperature for 1 hour. It was diluted with 30 ml ethyl acetate, washed sequencially with 20 ml 1N HCl, 20 ml 5% KOH and 20 ml brine. The organics were dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel column eluted with 1:2 to 1:1 ethyl acetate/hexane to give desired product as sticky material.

Workup

  1. washwashed sequencially with 20 ml 1N HCl, 20 ml 5% KOH and 20 ml brine
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel column
  6. washeluted with 1:2 to 1:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-87b1b195b3e740f4889ee5b1a7087cdf
Source dataset
uspto-grants-2012_11
Patent number
US08304434B2

Reaction notes

Loading…