Diisopropylethylamine → HCID 21100267, compound

HRID 1352277Notes

Reaction equation

HRID 1352277 reaction equation
[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][C:6]=1[C:7]([OH:9])=O)([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[Br:49][C:50]1[S:54][C:53]([N:55]2[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]2)=[N:52][CH:51]=1>O1CCCC1.C(OCC)(=O)C.CCCCCCC>[Br:49][C:50]1[S:54][C:53]([N:55]2[CH2:56][CH2:57][N:58]([C:7]([C:6]3[CH:10]=[C:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:12]=[CH:13][C:5]=3[O:4][CH:1]([CH3:2])[CH3:3])=[O:9])[CH2:59][CH2:60]2)=[N:52][CH:51]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 184230061-(5-Bromo-1,3-thiazol-2-yl)piperazineHCID 211002372-Isopropoxy-5-methylsulfonylbenzoic acid

Product 1

HCID 21100267HCID 21100267, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

To a solution of 0.31 mmol 2-isopropoxy-5-methanesulfonyl-benzoic acid (Example A1) in 7 ml tetrahydrofuran were added successively 0.46 mmol TBTU, 1.24 mmol N-ethyldiisopropylamine and 0.34 mmol 1-(5-bromo-thiazol-2-yl)-piperazine. The reaction mixture was stirred at RT for 16 h and then concentrated in vacuo. Chromatography (SiO2, ethyl acetate/heptane) afforded the title compound as a white foam (yield 87%). MS (m/e): 490.3 ({81Br}M+H+, 100%), 488.3 ({79Br}M+H+, 84%).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-033b7f7342314271b0d3fd3da885a407
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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