Hydrochloric Acid → BMY-25368 hydrochloride

HRID 1651423Notes

Reaction equation

HRID 1651423 reaction equation
[NH2:1][C:2]1[C:5](=[O:6])[C:4](=[O:7])[C:3]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:14]=1.[ClH:26]>CC(O)C>[ClH:26].[NH2:1][C:2]1[C:5](=[O:6])[C:4](=[O:7])[C:3]=1[NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 135156Bmy 25368

Product 1

HCID 6917814BMY-25368 hydrochlorideYield 56.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1-amino-2-[3-(3-piperidinomethylphenoxy)-propylamino]-1-cyclobutene-3,4-dione [prepared in Step A] (2.68 g, 0.0078 mole), 2-propanol (8.5 mL), and 1M aqueous hydrochloric acid (8.0 mL, 0.008 mole) was heated to reflux with stirring. Insoluble material was removed by filtration and acetone (24 mL) was added to the hot solution. The mixture was stirred at ambient temperature for 18 hours, then cooled to 0° C. The solid was collected by filtration, washed with acetone:2-propanol (2:1) (3 mL), and dried in vacuo to give 1.67 g (56.4% yield) of the title compound as an off-white powder. The product was shown by spectral data to be identical to authentic sample of the hydrochloride salt.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customInsoluble material was removed by filtration and acetone (24 mL)
  4. additionwas added to the hot solution
  5. stirringThe mixture was stirred at ambient temperature for 18 hours
  6. filtrationThe solid was collected by filtration
  7. washwashed with acetone:2-propanol (2:1) (3 mL)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-3f0c570a858446b3a8aa2fb8c3c3a6b0
Source dataset
uspto-grants-1990_05
Patent number
US04927970

Reaction notes

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