Water → HCID 67708522, compound

HRID 232978Notes

Reaction equation

HRID 232978 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]3[N:35]=[C:36]([CH3:39])O[CH:38]=3)[CH:31]=[C:32]([CH3:33])[C:6]=2[N:5]=1)[CH2:2][CH3:3].CN.[CH3:42][NH:43]C=O.O>C(O)(=O)C>[OH2:23].[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[N:35]=[C:36]([CH3:39])[N:43]([CH3:42])[CH:38]=3)[CH:31]=[C:32]([CH3:33])[C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 31254N-MethylformamideHCID 67708423HCID 67708423, compound

Product 1

HCID 67708522HCID 67708522, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.5 g (3 mMol) of tert.butyl 4'-[(2-n-propyl-4-methyl-6-(2-methyl-oxazol-4-yl)-benzimidazol-1-yl)-methyl]-biphenyl-2-carboxylate, 10 ml of 40% N-methylamine solution and 15 ml of N-methylformamide is heated for 10 hours to 200° C. in an autoclave. After cooling, the contents of the autoclave are stirred with about 40 ml of water, this suspension is adjusted to pH 6.5 with glacial acetic acid, then the crude product precipitated is suction filtered and dissolved in 1N sodium hydroxide solution. This solution is washed successively with 25 ml of acetic acid and diethylether, then adjusted to pH 6 with 20% citric acid. The product precipitated is suction filtered, washed with about 30 ml of water and dried, then triturated with diethylether and dried in a high vacuum.

Workup

  1. temperatureis heated for 10 hours to 200° C. in an autoclave
  2. temperatureAfter cooling
  3. customthe crude product precipitated
  4. filtrationfiltered
  5. dissolutiondissolved in 1N sodium hydroxide solution
  6. washThis solution is washed successively with 25 ml of acetic acid and diethylether
  7. customThe product precipitated
  8. filtrationfiltered
  9. washwashed with about 30 ml of water
  10. customdried
  11. customtriturated with diethylether
  12. customdried in a high vacuum

Sources & evidence

ORD record
ord-67c4ccbbf915463db595297d911309c4
Source dataset
uspto-grants-1997_01
Patent number
US05591762

Reaction notes

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