Diisopropylethylamine → HCID 86587979, compound

HRID 353060Notes

Reaction equation

HRID 353060 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:18]=[C:17]([S:19](=[O:24])(=[O:23])[N:20]([CH3:22])[CH3:21])[CH:16]=[CH:15][C:11]=1[C:12](O)=[O:13].[O:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[O:31][NH2:32].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>O1CCCC1.ClCCl>[O:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[O:31][NH:32][C:12](=[O:13])[C:11]1[CH:15]=[CH:16][C:17]([S:19](=[O:24])(=[O:23])[N:20]([CH3:22])[CH3:21])=[CH:18][C:10]=1[NH:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 22707299HCID 22707299, compound

Product 1

HCID 86587979HCID 86587979, compound

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

A solution comprised of 2-(2-chloro-4-iodo-phenylamino)-4-dimethylsulfamoyl-benzoic acid, O-(tetrahydro-2H-pyran-2-yl)-hydroxylamine (1.25 molar equivalents), benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (1.25 molar equivalents), and diisopropylethylamine (3 molar equivalents) in 1:1 v/v tetrahydrofuran-dichloromethane is stirred for 30 minutes. The reaction mixture is concentrated in vacuo and the residue is purified by flash chromatography; elution with dichloromethane affords the desired product. The product may be recrystallized with an appropriate solvent like methanol if further purification is necessary.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customthe residue is purified by flash chromatography
  3. washelution with dichloromethane

Sources & evidence

ORD record
ord-935a400c77c54f71afca8d60881390e2
Source dataset
uspto-grants-2004_06
Patent number
US06750217B2

Reaction notes

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