Diisopropylethylamine → HCID 58930368, compound

HRID 852432Notes

Reaction equation

HRID 852432 reaction equation
CN([CH:4]=[N:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:10]=1)=[S:7])C.[F:19][C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[C:22](=[O:25])[CH2:23]Br.C(N(C(C)C)CC)(C)C>CN(C=O)C>[F:19][C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[C:22]([C:23]1[S:7][C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([S:15]([CH3:18])(=[O:16])=[O:17])[CH:10]=2)=[N:5][CH:4]=1)=[O:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27374492-Bromo-2'-fluoroacetophenoneHCID 724664321-Dimethylaminomethylene-3-(3-methanesulfonyl-phenyl)-thiourea

Product 1

HCID 58930368HCID 58930368, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 37 mg (0.13 mmol) 1-Dimethylaminomethylene-3-(3-methanesulfonyl-phenyl)-thiourea in 0.33 ml DMF was added 28 mg (0.13 mmol) 2-Fluorophenacyl bromide and the mixture was allowed to stir at room temperature for 16 h. 17 mg (0.13 mmol) diisopropylethylamine was added and the mixture was subjected to preparative HPLC separation on reversed phase eluting with an acetonitrile/water gradient to yield 38.5 mg (79%) of the title compound after evaporation of the product fractions.

Workup

  1. customHPLC separation on reversed phase
  2. washeluting with an acetonitrile/water gradient

Sources & evidence

ORD record
ord-fdb8a297940f4ff0b53f4ac12f606c42
Source dataset
uspto-grants-2007_08
Patent number
US07253197B2

Reaction notes

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