Diisopropylethylamine → HCID 67497930, compound

HRID 1628244Notes

Reaction equation

HRID 1628244 reaction equation
Cl.Cl.[CH3:3][N:4]1[C:8]([NH:9][C:10](=[O:26])[C@@H:11]([NH:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][C:6]([C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)=[N:5]1.CCN(C(C)C)C(C)C>[Pd].CO>[CH3:3][N:4]1[C:8]([NH:9][C:10](=[O:26])[C@@H:11]([NH:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:7][C:6]([C:27]2[CH:28]=[CH:29][N:30]=[CH:31][CH:32]=2)=[N:5]1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 86664825HCID 86664825, compound

Product 1

HCID 67497930HCID 67497930, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a 250 ml flask was added 6.3 g of (S)-ethyl 2-(1-(1-methyl-3-(pyridin-4-yl)-1H-pyrazol-5-ylamino)-1-oxo-3-phenylpropan-2-ylamino)acetate 1.F, 1.8 g of Pd on carbon, 150 ml of MeOH and 2.8 ml of DIEA. 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 4.5 g of (S)-ethyl 2-(1-(1-methyl-3-(pyridin-4-yl)-1H-pyrazol-5-ylamino)-1-oxo-3-phenylpropan-2-ylamino)acetate as a sticky solid.

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-ce2d5a7e1edc4ba29da1cbf850346ee1
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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