Ethyl Acetate → HCID 68580205, compound

HRID 2234039Notes

Reaction equation

HRID 2234039 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[C:16]([Cl:17])=[C:15]([CH3:18])[NH:14][C:13]=1[C:19]([NH:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]2[O:32][C:31]([C:33](OC)=[O:34])=[N:30][N:29]=2)[CH2:24][CH2:23]1)=[O:20].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+].CCOC(C)=O>C1COCC1>[Cl:11][C:12]1[C:16]([Cl:17])=[C:15]([CH3:18])[NH:14][C:13]=1[C:19]([NH:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]2[O:32][C:31]([CH2:33][OH:34])=[N:30][N:29]=2)[CH2:24][CH2:23]1)=[O:20]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 68579602HCID 68579602, compound

Product 1

HCID 68580205HCID 68580205, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisobutylaluminum hydride (0.94 ml, 1 M solution in toluene, 0.94 mmol) was added dropwise to a solution of methyl 5-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3,4-oxadiazole-2-carboxylate (Example 302) (95 mg, 0.24 mmol) in THF (8 ml) at 0° C. The resultant mixture was allowed to slowly warm to room temperature and was stirred overnight. Potassium sodium tartrate (15 ml, 10% aqueous solution) and EtOAc (100 ml) were added to the reaction mixture and the resultant mixture was stirred vigorously for 1 h. The organic phase was separated, dried over sodium sulfate, filtered and concentrated. The crude residue was purified by preparative reversed-phase HPLC (water/acetonitrile gradient, 10-95%) to yield 45 mg of the title compound.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by preparative reversed-phase HPLC (water/acetonitrile gradient, 10-95%)

Sources & evidence

ORD record
ord-46615684599e44f885d8fab67f7cc783
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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