HCID 69843622, compound → HCID 69844447, compound

HRID 617815Notes

Reaction equation

HRID 617815 reaction equation
[ClH:1].[CH3:2][N:3]([CH3:32])[CH2:4][CH2:5][N:6]1[C:29](=[O:30])[C:10]2[CH:11]=[C:12]([N+:26]([O-])=O)[CH:13]=[C:14]3[O:15][C:16]4[CH:17]=[C:18]5[CH:25]=[CH:24][CH:23]=[CH:22][C:19]5=[CH:20][C:21]=4[N:8]([C:9]=23)[C:7]1=[O:31].[H][H]>C(O)(=O)C.[C].[Pd]>[ClH:1].[ClH:1].[NH2:26][C:12]1[CH:13]=[C:14]2[C:9]3=[C:10]([C:29](=[O:30])[N:6]([CH2:5][CH2:4][N:3]([CH3:2])[CH3:32])[C:7](=[O:31])[N:8]3[C:21]3[CH:20]=[C:19]4[CH:22]=[CH:23][CH:24]=[CH:25][C:18]4=[CH:17][C:16]=3[O:15]2)[CH:11]=1

Participants

5

Reactant 2

HCID 69843622HCID 69843622, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69844447HCID 69844447, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

268 mg (0.641 mmol) of the free base of the compound of Example 27 was dissolved in acetic acid (10 ml) and 10% palladium-carbon was added thereto. Then catalytic reduction was effected at room temperature in a hydrogen atmosphere. After filtering off the palladium-carbon through celite, the filtrate was concentrated. Next, water and a saturated aqueous solution of sodium hydrogencarbonate were added thereto and the obtained mixture was stirred at room temperature. The precipitate was recovered by filtration, washed with water and suspended in methanol. After adding conc. hydrochloric acid thereto, the obtained mixture was stirred at room temperature. Thus it turned into a homogeneous solution and then a precipitate was formed. The precipitate was recovered by filtration to thereby give 179 mg of the title compound.

Workup

  1. filtrationAfter filtering off the palladium-carbon through celite
  2. concentrationthe filtrate was concentrated
  3. additionNext, water and a saturated aqueous solution of sodium hydrogencarbonate were added
  4. filtrationThe precipitate was recovered by filtration
  5. washwashed with water
  6. additionAfter adding conc. hydrochloric acid
  7. stirringthe obtained mixture was stirred at room temperature
  8. customa precipitate was formed
  9. filtrationThe precipitate was recovered by filtration

Sources & evidence

ORD record
ord-dda7646feee446838647326d8d250069
Source dataset
uspto-grants-1999_09
Patent number
US05952335

Reaction notes

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