HCID 67708492, compound → HCID 53963344, compound

HRID 234027Notes

Reaction equation

HRID 234027 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[C:17]([C:22]([O:24]C(C)(C)C)=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:12][CH:11]=2)[C:7]2[CH:29]=[C:30]([C:34]([NH:36][CH:37]([C:41](=O)[CH3:42])[CH:38]([CH3:40])[CH3:39])=[O:35])[CH:31]=[C:32]([CH3:33])[C:6]=2[N:5]=1)[CH2:2][CH3:3]>P(Cl)(Cl)(Cl)=O>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[C:17]([C:22]([OH:24])=[O:23])=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:14][CH:15]=2)[C:7]2[CH:29]=[C:30]([C:34]3[O:35][C:41]([CH3:42])=[C:37]([CH:38]([CH3:40])[CH3:39])[N:36]=3)[CH:31]=[C:32]([CH3:33])[C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

3

Reactant 1

HCID 67708492HCID 67708492, compound

Product 1

HCID 53963344HCID 53963344, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
105 °C

Procedure

3.9 g (6.7 mMol) of tert.butyl 4'-[[2-n-propyl-4-methyl-6-[N-(1-acetyl-2-methyl-n-propyl)-aminocarbonyl]-1H-benzimidazol-1-yl]-methyl]-biphenyl-2-carboxylate are dissolved in 50 ml of phosphorusoxychloride and stirred for 2.5 hours at 105° C. Then the phosphorusoxychloride is removed, the residue is decomposed with water at 80° C. and, after cooling, mixed with conc. ammonia. The pH is adjusted to 5 by the addition of glacial acetic acid, the precipitate thus formed is suction filtered, washed with water, taken up in methylene chloride/methanol (9:1) and dried over magnesium sulphate. The crude product is chromatographed on silica gel (particle size: 0.032-0.063 mm) using as eluant petroleum ether/ethyl acetate/glacial acetic acid (1:1:0.002) and methylene chloride/ethanol/glacial acetic acid (20:1:0.002). The uniform fractions are combined, evaporated down, triturated with ether and suction filtered.

Workup

  1. customThen the phosphorusoxychloride is removed
  2. customis decomposed with water at 80° C.
  3. temperatureafter cooling
  4. additionmixed with conc. ammonia
  5. additionThe pH is adjusted to 5 by the addition of glacial acetic acid
  6. customthe precipitate thus formed
  7. filtrationfiltered
  8. washwashed with water
  9. dry with materialdried over magnesium sulphate
  10. customThe crude product is chromatographed on silica gel (particle size: 0.032-0.063 mm)
  11. customevaporated down
  12. customtriturated with ether and suction
  13. filtrationfiltered

Sources & evidence

ORD record
ord-ae9dabe6371043ab9acdd32f49dae9a3
Source dataset
uspto-grants-1997_01
Patent number
US05594003

Reaction notes

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