HCID 90416684, compound → HCID 90416939, compound

HRID 633582Notes

Reaction equation

HRID 633582 reaction equation
C([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[F:24])=[C:12]([C:25]2[C:33]3[C:28](=[C:29]([O:34][CH3:35])[N:30]=[CH:31][CH:32]=3)[N:27]([CH3:36])[CH:26]=2)[CH:11]=1)C1C=CC=CC=1>O1CCCC1.[OH-].[OH-].[Pd+2]>[F:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH2:8])=[CH:11][C:12]=1[C:25]1[C:33]2[C:28](=[C:29]([O:34][CH3:35])[N:30]=[CH:31][CH:32]=2)[N:27]([CH3:36])[CH:26]=1

Participants

4

Reactant 1

HCID 90416684HCID 90416684, compound

Product 1

HCID 90416939HCID 90416939, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 106A (78 mg, 0.161 mmol) in tetrahydrofuran (10 mL) was added to 20% palladium hydroxide on carbon (16 mg, 0.012 mmol) in a 50 mL pressure bottle and the mixture was stirred for 16 hours under a hydrogen atmosphere (30 psi). The mixture was filtered through a nylon membrane and concentrated. The residue was purified by flash column chromatography (silica gel, 0-5% 7N methanolic ammonia in dichloromethane) to afford the title compound (57 mg, 90% yield).

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationconcentrated
  3. customThe residue was purified by flash column chromatography (silica gel, 0-5% 7N methanolic ammonia in dichloromethane)

Sources & evidence

ORD record
ord-8e31b7e64b9f4c0ca127ab5b86c37b23
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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