Diisopropylethylamine → HCID 25255787, compound

HRID 1873857Notes

Reaction equation

HRID 1873857 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:11]([CH3:14])(=[O:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH3:15][C:16]([CH:31]1[CH2:34][NH:33][CH2:32]1)([S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1)(=[O:20])=[O:19])[CH3:17].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>CS(C)=O.O.FC(F)(F)C(O)=O.CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:11]([CH3:14])(=[O:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([N:33]1[CH2:34][CH:31]([C:16]([CH3:17])([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=2)(=[O:19])=[O:20])[CH3:15])[CH2:32]1)=[O:9]

Participants

9

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27827355-Fluoro-2-(methylsulfonyl)benzoic acidHCID 59447445HCID 59447445, compound

Product 1

HCID 25255787HCID 25255787, compound

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a 10 ml vial was added 5-fluoro-2-(methylsulfonyl)benzoic acid (35.5 mg, 0.163 mmol), 3-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)azetidine (50 mg, 0.163 mmol), Bop reagent (79 mg, 0.179 mmol), diisopropylethyl amine (0.142 ml, 0.813 mmol) and 1 ml dimethylformamide. The resulting solution was stirred at room temperature for 1 hour. It was diluted with 1 m dimethyl sulfoxide, 0.5 ml water and 0.1 ml trifluoroacetic acid. This mixture was loaded on to reverse phase column directly eluted with water acetonitrile gradient solvent to give the title compound as a fluffy white solid after lyophilizing.

Workup

  1. washdirectly eluted with water acetonitrile gradient solvent

Sources & evidence

ORD record
ord-76f8fb7cc58e4a31bf16d136a227ebca
Source dataset
uspto-grants-2012_11
Patent number
US08304434B2

Reaction notes

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