HCID 66587916, compound → HCID 66587919, compound

HRID 1469148Notes

Reaction equation

HRID 1469148 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]([CH2:19][C:20]([N:22]2[CH2:42][CH2:41][C:25]3[C:26]4[C:27]([N:32]([CH2:33][C:34]5[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=5)[C:24]=3[CH2:23]2)=[N:28][CH:29]=[CH:30][CH:31]=4)=[O:21])[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])C1C=CC=CC=1.[H][H]>[C].[Pd].CO.C1COCC1>[F:40][C:36]1[CH:35]=[C:34]([CH:39]=[CH:38][CH:37]=1)[CH2:33][N:32]1[C:27]2=[N:28][CH:29]=[CH:30][CH:31]=[C:26]2[C:25]2[CH2:41][CH2:42][N:22]([C:20](=[O:21])[CH2:19][C:17]3[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([OH:8])[CH:18]=3)[CH2:23][C:24]1=2

Participants

5

Reactant 2

HCID 66587916HCID 66587916, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66587919HCID 66587919, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To 1.24 mL of a methanol/THF (1:1) solution of the compound (70 mg) produced in Example 63 was added 5% palladium carbon (7 mg, 10 wt %), and the mixture was stirred at room temperature for 3 hours under the hydrogen atmosphere. After the reaction solution was filtered with Celite, the solvent was concentrated under reduced pressure. The resulting residue was purified by silica gel column (hexane/ethyl acetate=70:30-40:60) to obtain the title compound (55.2 mg) having the following physical property values.

Workup

  1. filtrationAfter the reaction solution was filtered with Celite
  2. concentrationthe solvent was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column (hexane/ethyl acetate=70:30-40:60)

Sources & evidence

ORD record
ord-cc2a0c344fe74ba8b396818200b312d5
Source dataset
uspto-grants-2015_04
Patent number
US09006246B2

Reaction notes

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