HCID 86635444, compound → HCID 86635443, compound

HRID 2353449Notes

Reaction equation

HRID 2353449 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@@H:14]([C:15]2[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:16]=2[F:23])[CH2:13][CH2:12][C@H:11]([N:24]2[CH2:31][C:30]3[C:29]([NH:32]C(=O)OCC4C=CC=CC=4)=[N:28][NH:27][C:26]=3[CH2:25]2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[NH2:32][C:29]1[C:30]2[CH2:31][N:24]([C@@H:11]3[CH2:10][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C@@H:14]([C:15]4[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:16]=4[F:23])[CH2:13][CH2:12]3)[CH2:25][C:26]=2[NH:27][N:28]=1

Participants

4

Reactant 1

HCID 86635444HCID 86635444, compound

Product 1

HCID 86635443HCID 86635443, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To 31 mg (0.05 mmol) of the product from Step A in 4 mL of methanol was added 10 mg of 20% palladium hydroxide on carbon. The reaction mixture was purged with hydrogen gas and held under 1 atmosphere of hydrogen for 1 h. The mixture was filtered through a pad of Celite and the filter cake was successively washed with three portions of 4 mL of methanol. The combined filtrate and washings were concentrated and used without further purification in Step C. LC/MS 452.2 (M+1).

Workup

  1. customThe reaction mixture was purged with hydrogen gas
  2. filtrationThe mixture was filtered through a pad of Celite
  3. washthe filter cake was successively washed with three portions of 4 mL of methanol
  4. concentrationThe combined filtrate and washings were concentrated
  5. customused without further purification in Step C

Sources & evidence

ORD record
ord-8f19412660f54bdca417a7b9128341bf
Source dataset
uspto-grants-2010_07
Patent number
US07750034B2

Reaction notes

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