HCID 67411071, compound → HCID 59614552, compound

HRID 912626Notes

Reaction equation

HRID 912626 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]3[C:24]=2[N:23]=[CH:22][C:21]([C:25]2[CH:30]=[CH:29][C:28]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:27][CH:26]=2)=[CH:20]3)=[CH:13][C:12]([F:42])=[C:11]([O:43][CH3:44])[N:10]=1)C1C=CC=CC=1.[H][H]>[Pd].CCOC(C)=O>[C:38]([C:17]1[C:18]([O:36][CH3:37])=[C:19]2[C:24](=[C:15]([C:14]3[C:9](=[O:8])[NH:10][C:11]([O:43][CH3:44])=[C:12]([F:42])[CH:13]=3)[CH:16]=1)[N:23]=[CH:22][C:21]([C:25]1[CH:26]=[CH:27][C:28]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:29][CH:30]=1)=[CH:20]2)([CH3:41])([CH3:39])[CH3:40]

Participants

5

Reactant 2

HCID 67411071HCID 67411071, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59614552HCID 59614552, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

step 5—A mixture of 148 (0.100 g, 0.162 mmol), Pd/C (30 mg) and EtOAc was stirred under one atmosphere hydrogen for 20 h. The catalyst was filtered and washed with EtOAc. The filtrate was concentrated and the crude product purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (30 to 80% EtOAc) to afford 25 mg (29.3%) of I-47.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. customthe crude product purified by SiO2 chromatography
  5. washeluting with an EtOAc/hexane gradient (30 to 80% EtOAc)
  6. customto afford 25 mg (29.3%) of I-47

Sources & evidence

ORD record
ord-e5950c513d804922bd5d2a5a97114f6a
Source dataset
uspto-grants-2011_09
Patent number
US08026253B2

Reaction notes

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