HCID 66941896, compound → HCID 21084458, compound

HRID 348688Notes

Reaction equation

HRID 348688 reaction equation
C(OC(=O)[N:10]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:46])[C:26]2[CH:31]=[CH:30][C:29]([CH2:32][N:33]([CH2:40][C:41]3[NH:42][CH:43]=[CH:44][N:45]=3)[CH2:34][C:35]3[NH:36][CH:37]=[CH:38][N:39]=3)=[CH:28][CH:27]=2)=[CH:20][CH:19]=1)[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)C1C=CC=CC=1.[H][H]>CO.C(O)C.[C].[Pd]>[NH:36]1[CH:37]=[CH:38][N:39]=[C:35]1[CH2:34][N:33]([CH2:32][C:29]1[CH:30]=[CH:31][C:26]([C:25]([NH:24][C:21]2[CH:22]=[CH:23][C:18]([CH2:17][NH:10][CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)=[CH:19][CH:20]=2)=[O:46])=[CH:27][CH:28]=1)[CH2:40][C:41]1[NH:45][CH:44]=[CH:43][N:42]=1

Participants

6

Reactant 2

HCID 66941896HCID 66941896, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21084458HCID 21084458, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

The compound (282 mg) obtained in Example 88-1 was dissolved in methanol (14 ml). After having been cooled with ice, the solution was added with a suspension of 10% palladium-carbon (140 mg) in ethanol (3.0 ml). After having been subjected to hydrogen displacement, the mixture was stirred under a hydrogen atmosphere at room temperature for 3 hours. After the reaction, the reaction solution was filtrated through Celite and the solvent was then distilled off. Then, the residue was purified through silica gel column chromatography (chloroform/methanol/water) and treated with hydrochloric acid, thereby obtaining hydrochloride (47.1 mg) of the subject compound as a white solid.

Workup

  1. temperatureAfter having been cooled with ice
  2. customAfter the reaction
  3. filtrationthe reaction solution was filtrated through Celite
  4. distillationthe solvent was then distilled off
  5. customThen, the residue was purified through silica gel column chromatography (chloroform/methanol/water)
  6. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-053fb284ef294fa8b035504286a9b10b
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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