HCID 86634383, compound → HCID 86634384, compound

HRID 1191284Notes

Reaction equation

HRID 1191284 reaction equation
[N:1]1([C:8]2[CH:13]=[C:12](Cl)[N:11]=[C:10]([NH:15][CH:16]3[CH2:21][CH2:20][CH2:19][N:18](C(OCC4C=CC=CC=4)=O)[CH:17]3[CH2:32][CH2:33][NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[N:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[C].[Pd].C(O)(=O)C>[N:1]1([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:15][CH:16]3[CH2:21][CH2:20][CH2:19][NH:18][CH:17]3[CH2:32][CH2:33][NH:34][C:35](=[O:36])[O:37][C:38]([CH3:40])([CH3:39])[CH3:41])[N:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 86634383HCID 86634383, compound

Product 1

HCID 86634384HCID 86634384, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

The compound 19 (225 mg), acetic acid (4 mL) and 10% palladium carbon (20 mg) were stirred under hydrogen atmosphere at room temperature for 6 hours. The reaction solution was filtered and then the filtrate was concentrated. The residue was added aqueous 2N sodium hydroxide solution and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate, concentrated and obtained the title compound (155 mg) having the following physical properties.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated
  3. additionThe residue was added aqueous 2N sodium hydroxide solution
  4. extractionextracted with dichloromethane
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1c1a52cd76354de99a7d18f1a27f009e
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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