Diisopropylethylamine → HCID 67497107, compound

HRID 1628246Notes

Reaction equation

HRID 1628246 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:12]=[C:11]([NH:13][C:14](=[O:32])[C@@H:15]([NH:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:10]([CH3:33])[N:9]=2)[CH:5]=[CH:4][N:3]=1.C(N(C(C)C)CC)(C)C>[Pd].CO>[CH3:33][N:10]1[C:11]([NH:13][C:14](=[O:32])[C@@H:15]([NH:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:12][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[CH:2][CH:7]=2)=[N:9]1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 86762560HCID 86762560, compound

Product 1

HCID 67497107HCID 67497107, compoundYield 61.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a 100 ml flask was added 1.4 g of 17.8.A, 500 mg of Pd on carbon, 150 ml of MeOH and 520 μl of diisopropylethylamine. The air was removed from the flask and replaced with hydrogen gas. This process was repeated four more times and then the reaction was stirred at room temperature for 2 hours, at which time the reaction was filtered over a bed of celite. The solvent was then removed and the crude was purified with a silica gel column (eluting with 2-5% MeOH in DCM) to give 800 mg of (S)-tert-butyl 2-(1-(1-methyl-3-(pyridin-4-yl)-1H-pyrazol-5-ylamino)-1-oxo-3-phenylpropan-2-ylamino)acetate 17.8.B as a solid. (Rf silica=0.27 in 5% MeOH in DCM).

Workup

  1. customThe air was removed from the flask
  2. filtrationwas filtered over a bed of celite
  3. customThe solvent was then removed
  4. customthe crude was purified with a silica gel column (eluting with 2-5% MeOH in DCM)

Sources & evidence

ORD record
ord-399b9f86e72840ad942975fbdeba62e4
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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