Methanol → HCID 20086967, compound

HRID 1608652Notes

Reaction equation

HRID 1608652 reaction equation
C(OC[N:10]1[C:15](=[O:16])[C:14]([NH:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[CH:28][CH:27]=2)[CH3:22])=[C:13]([Cl:37])[CH:12]=[N:11]1)C1C=CC=CC=1.B(Br)(Br)Br.CO.O>C1C=CC=CC=1>[Cl:37][C:13]1[CH:12]=[N:11][NH:10][C:15](=[O:16])[C:14]=1[NH:17][CH2:18][CH2:19][CH2:20][N:21]([CH2:23][CH2:24][O:25][C:26]1[CH:27]=[CH:28][C:29]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[CH:30][CH:31]=1)[CH3:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25134Boron tribromideHCID 20086985HCID 20086985, compound

Product 1

HCID 20086967HCID 20086967, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2.69 g (4.88 mmoles) of the compound of Example 44 are dissolved in 53 ml of anhydrous benzene. 2.92 ml of boron tribromide are dropped to the solution so that the temperature of the reaction mixture should not exceed 20° C. The suspension thus obtained is stirred at room temperature for half an hour. Then 40 ml of methanol are dropped under stirring and cooling with icy water at such a rate that the inner temperature should not exceed 25° C. The reaction mixture is evaporated, the residue is boiled with 68 ml of distilled water for 1 hour, the solution is cooled, diluted with 100 ml of distilled water, the pH is adjusted with solid potassium hydrogen carbonate to neutral and the solution is extracted with chloroform. The organic phase is dried and evaporated, then the residue is purified by column chromatography. Thus 1.01 g (48%) of the desired compound are obtained. Rf =0.45. Its monohydrochloride salt melts at 181°-183° C.

Workup

  1. customexceed 20° C
  2. customThe suspension thus obtained
  3. stirringunder stirring
  4. customexceed 25° C
  5. customThe reaction mixture is evaporated
  6. temperaturethe solution is cooled
  7. additiondiluted with 100 ml of distilled water
  8. extractionis extracted with chloroform
  9. customThe organic phase is dried
  10. customevaporated
  11. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-42be1c0573a64ddd815b86845757b254
Source dataset
uspto-grants-1995_03
Patent number
US05395934

Reaction notes

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