Ethyl Acetate → HCID 86596373, compound

HRID 1373198Notes

Reaction equation

HRID 1373198 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12].[F:13][C:14]1([C:33](O)=[O:34])[C:23]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=2[F:32])=[CH:22][C:17]2=[N:18][CH2:19][N:20]([CH3:21])[C:16]2=[CH:15]1.C1(N=C=NC2CCCCC2)CCCCC1.CCOC(C)=O>C1COCC1>[F:1][C:2]1[C:7]([O:8][C:33]([C:14]2([F:13])[C:23]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=3[F:32])=[CH:22][C:17]3=[N:18][CH2:19][N:20]([CH3:21])[C:16]3=[CH:15]2)=[O:34])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 68805556HCID 68805556, compound

Product 1

HCID 86596373HCID 86596373, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of pentafluorophenol (21.6 g, 0.113 mol) DMF (100 ml) at room temperature was slowly added to a suspension of 5-fluoro-6-(2-fluoro-4-iodo-phenylamino)-3-methyl-3H-benzoimidazole-5-carboxylic acid (40.0 g , 0.093 mol) in 165 ml of THF, followed by dicyclohexylcarbodiimide (24.14 g, 0.118 mol). The mixture was stirred overnight at room temperature (TLC-EtOAc), evaporated under vacuum and is added 200 g of crushed ice to the residual DMF solution. The light yellow compound separated was filtered and vacuum dried to give the title compound (crude), which is directly proceeded to next step without purification. Yield: 55 g (99%).

Workup

  1. customevaporated under vacuum
  2. additionis added 200 g of crushed ice to the residual DMF solution
  3. customThe light yellow compound separated
  4. filtrationwas filtered
  5. customvacuum dried

Sources & evidence

ORD record
ord-88a01299cd984862879acf96519c67d4
Source dataset
uspto-grants-2007_01
Patent number
US07160915B2

Reaction notes

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