Diisopropylethylamine → HCID 178427889, compound

HRID 1795882Notes

Reaction equation

HRID 1795882 reaction equation
[F:1][C:2]1[C:7]2[NH:8][CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([C:11]([OH:13])=O)[C:3]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=1[CH3:22].[O:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[O:29][NH2:30].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:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[O:29][NH:30][C:11]([C:4]1[C:3]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=2[CH3:22])=[C:2]([F:1])[C:7]2[NH:8][CH:9]=[N:10][C:6]=2[CH:5]=1)=[O:13]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 178427892HCID 178427892, compound

Product 1

HCID 178427889HCID 178427889, compound

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

A solution comprised of 7-fluoro-6-(4-iodo-2-methyl-phenylamino)-1H-benzoimidazole-5-carboxylic acid, O-(tetrahydro-2H-pyran-2-yl)-hydroxylamine (1.25 equiv.), benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (1.25 equiv.), and a diisopropylethylamine (3 equiv.) 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-3f488b00a2384725a1c3a4192268e50a
Source dataset
uspto-grants-2006_04
Patent number
US07030119B1

Reaction notes

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