HCID 67070043, compound → HCID 67070143, compound

HRID 2390871Notes

Reaction equation

HRID 2390871 reaction equation
C([O:8][C:9]1[C:14]([C:15]2[CH:16]=[C:17]([C:38]([CH3:41])([CH3:40])[CH3:39])[C:18]([O:36][CH3:37])=[C:19]([NH:21][C:22]([C:24]3[N:25]=[N:26][C:27]([NH:30][CH2:31][C:32]([F:35])([F:34])[F:33])=[CH:28][CH:29]=3)=[O:23])[CH:20]=2)=[CH:13][CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1>CO.CCOC(C)=O.[OH-].[OH-].[Pd+2]>[C:38]([C:17]1[C:18]([O:36][CH3:37])=[C:19]([NH:21][C:22]([C:24]2[N:25]=[N:26][C:27]([NH:30][CH2:31][C:32]([F:35])([F:33])[F:34])=[CH:28][CH:29]=2)=[O:23])[CH:20]=[C:15]([C:14]2[C:9](=[O:8])[NH:10][CH:11]=[CH:12][CH:13]=2)[CH:16]=1)([CH3:41])([CH3:39])[CH3:40]

Participants

5

Reactant 1

HCID 67070043HCID 67070043, compound

Product 1

HCID 67070143HCID 67070143, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

step 3—To a solution of 314 (0.029 g, 0.1 mmol) in MeOH (5.0 mL) and EtOAc (4.0 mL) was added Pd(OH)2 (0.005 g). The solution was stirred under 1 atm of H2. After 18 h the mixture was filtered through a pad of CELITE and the filtrate concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with a MeOH/DCM gradient (1% to 10% MeOH) to 0.018 g (74%) of I-248 as an oil: MS (CI) mz/=476 (M+H).

Workup

  1. filtrationAfter 18 h the mixture was filtered through a pad of CELITE
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe crude product was purified by SiO2 chromatography
  4. washeluting with a MeOH/DCM gradient (1% to 10% MeOH) to 0.018 g (74%) of I-248 as an oil

Sources & evidence

ORD record
ord-3380382b98d445489067b5abe1aebf46
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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