Sodium Bicarbonate → HCID 86583567, compound

HRID 1790587Notes

Reaction equation

HRID 1790587 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:16]2[CH:21]=[C:20]([C:22]3[N:23](O)[C:24]([CH3:27])=[N:25][CH:26]=3)[CH:19]=[C:18]([O:29][CH2:30][CH3:31])[CH:17]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2].C([O-])(O)=O.[Na+]>O.CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:16]2[CH:21]=[C:20]([C:22]3[NH:23][C:24]([CH3:27])=[N:25][CH:26]=3)[CH:19]=[C:18]([O:29][CH2:30][CH3:31])[CH:17]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 86583568HCID 86583568, compound

Product 1

HCID 86583567HCID 86583567, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A 20% solution of TiCl3 in H2O was added dropwise at 0° C. to a solution of the ethyl (RS)-(4-cyano-phenylamino)-[3-ethoxy-5-(3-hydroxy-2-methyl-3H-imidazol-4-yl)-phenyl]-acetate (355 mg, 0.844 mmol) obtained in Example 247.1 in MeOH (4.2 ml). The mixture was stirred for 3 h. at room temperature, subsequently poured into NaHCO3 solution/ice-water and extracted with CH2Cl2. The organic phase was dried, filtered and concentrated. The residue was purified by chromatography (SiO2, CH2Cl2->CH2Cl2/MeOH 95:5). There were obtained 50 mg (15%) of ethyl (RS)-(4-cyano-phenylamino)-[3-ethoxy-5-(2-methyl-3H-imidazol-4-yl)-phenyl]-acetate as a yellowish solid; MS: 405 ([M+H]+).

Workup

  1. extractionextracted with CH2Cl2
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (SiO2, CH2Cl2->CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-d7fcac670a6c4fc5aef22f9d461d86f1
Source dataset
uspto-grants-2006_07
Patent number
US07071212B2

Reaction notes

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