Diisobutylaluminumhydride → HCID 68579603, compound

HRID 2234019Notes

Reaction equation

HRID 2234019 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:22][C:21]([C:23](OCC)=[O:24])=[N:20][N:19]=2)[CH2:14][CH2:13]1)=[O:10].[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:22][C:21]([CH2:23][OH:24])=[N:20][N:19]=2)[CH2:14][CH2:13]1)=[O:10]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 68580109HCID 68580109, compound

Product 1

HCID 68579603HCID 68579603, compoundYield 6.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 5-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3,4-thiadiazole-2-carboxylate (Example 219, 280 mg, 0.65 mmol) in THF (5 ml) was cooled to 0° C. and treated with diisobutylaluminium hydride (1.3 ml, 1.95 mmol) dropwise over 5 min. The reaction was kept in the ice bath and allowed to slowly warm to room temperature while stirring overnight. LC-MS indicated that the reaction was complete. The reaction was quenched with aqueous Rochelle salt, and the resultant mixture was diluted with EtOAc (10 ml) and stirred vigorously for 2 h. The layers were separated, and the aqueous portion was extracted with EtOAc. The combined organic portions were dried (Na2SO4), filtered, and concentrated to give a pale orange oil. The crude material was purified by preparatory HPLC (35-75% CH3CN/H2O, 0.1% TFA, 14 min.) to give 17 mg of the title compound.

Workup

  1. customThe reaction was quenched with aqueous Rochelle salt
  2. additionthe resultant mixture was diluted with EtOAc (10 ml)
  3. stirringstirred vigorously for 2 h
  4. customThe layers were separated
  5. extractionthe aqueous portion was extracted with EtOAc
  6. dry with materialThe combined organic portions were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a pale orange oil
  10. customThe crude material was purified by preparatory HPLC (35-75% CH3CN/H2O, 0.1% TFA, 14 min.)

Sources & evidence

ORD record
ord-fdd9786a8dc14ed38f87bfe72948f8fa
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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