Diisopropylethylamine → HCID 86587979, compound

HRID 2305336Notes

Reaction equation

HRID 2305336 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-e0becfe9badc45ed9ed806259d6b45ed
Source dataset
uspto-grants-2002_08
Patent number
US06440966B1

Reaction notes

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