Diisopropylethylamine → HCID 178427890, compound

HRID 992391Notes

Reaction equation

HRID 992391 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].Cl.[CH:24]1([CH2:27][O:28][NH2:29])[CH2:26][CH2:25]1.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>[CH:24]1([CH2:27][O:28][NH:29][C:11]([C:4]2[C:3]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=3[CH3:22])=[C:2]([F:1])[C:7]3[NH:8][CH:9]=[N:10][C:6]=3[CH:5]=2)=[O:13])[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 11557279O-(cyclopropylmethyl)hydroxylamine hydrochlorideHCID 178427892HCID 178427892, compound

Product 1

HCID 178427890HCID 178427890, 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-cyclopropylmethylhydroxylamine hydrochloride (1.25 equiv.), benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (1.25 equiv.), and 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 taken up into diethyl ether. The ether phase is washed with dilute aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, and brine, is dried (MgSO4), and is concentrated in vacuo to afford the desired product. The product may be recrystallized with an appropriate solvent like methanol or chloroform if further purification is necessary.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. washThe ether phase is washed with dilute aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, and brine
  3. dry with materialis dried (MgSO4)
  4. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-afa78a3f927b4ec0bda31000b01bfb16
Source dataset
uspto-grants-2002_10
Patent number
US06469004B1

Reaction notes

Loading…