HCID 68865807, compound → HCID 68864852, compound

HRID 1725891Notes

Reaction equation

HRID 1725891 reaction equation
[Br:1][C:2]1[C:3]([CH3:28])=[C:4]([C:15]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)(=[O:21])=[O:20])=[CH:16][CH:17]=1)[C:5]([O:7]CC1C=CC=CC=1)=[O:6]>CO.[Pd]>[Br:1][C:2]1[C:3]([CH3:28])=[C:4]([C:15]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)(=[O:21])=[O:20])=[CH:16][CH:17]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 1

HCID 68865807HCID 68865807, compound

Product 1

HCID 68864852HCID 68864852, compoundYield 6.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of Example 110A (150 mg, 0.32 mmol) in methanol (8 mL) was treated with 5% Pd/C (100 mg), stirred under a hydrogen atmosphere for 1 hour, and filtered through diatomaceous earth (Celite®). The filtrate was concentrated and purified by reverse-phase HPLC to provide the desired product (6.5 mg, 6.4%). 1H NMR (DMSO-d6) δ 2.31 (s, 3H), 6.99 (d, 1H), 7.58 (d, 1H), 7.69 (d, 1H), 7.88 (dd, 1H), 8.06 (dd, 1H), 8.72 (d, 1H), 10.08 (br s, 1H), 13.58 (br s, 1H); MS (ESI(−)) m/e 371 (M−H)−.

Workup

  1. filtrationfiltered through diatomaceous earth (Celite®)
  2. concentrationThe filtrate was concentrated
  3. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-dafcbf56502b4981a85eb4d13fd2544a
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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