HCID 18536176, compound → HCID 18536074, compound

HRID 412143Notes

Reaction equation

HRID 412143 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[N:19]2[CH2:24][CH2:23][N:22]([CH2:25][C:26]3[N:30]([CH2:31][C:32]4[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[C:34]([F:40])[CH:33]=4)[C:29]([CH3:41])=[N:28][CH:27]=3)[CH2:21][C:20]2=[O:42])=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>CO.CCOC(C)=O.[Pd]>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[N:19]2[CH2:24][CH2:23][N:22]([CH2:25][C:26]3[N:30]([CH2:31][C:32]4[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[C:34]([F:40])[CH:33]=4)[C:29]([CH3:41])=[N:28][CH:27]=3)[CH2:21][C:20]2=[O:42])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 18536176HCID 18536176, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18536074HCID 18536074, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of the benzyl ether from Step B (419 mg, 0.75 mmol) in 6 mL of 1:1 MeOH/EtOAc was added 10% palladium on carbon (250 mg). The solution was stirred under a balloon atmosphere of hydrogen at room temperature. After 4 hours, another portion of Pd/C was added (250 mg). After 16 hours, the solution was filtered through celite. Concentration in vacuo provided the titled product which was used in the next reaction without further purification.

Workup

  1. waitAfter 16 hours
  2. filtrationthe solution was filtered through celite
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-cc4e64157547442794e5fd2f5e4e57d1
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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