Ethanol → HCID 67497272, compound

HRID 1628336Notes

Reaction equation

HRID 1628336 reaction equation
[NH2:1][C@@H:2]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:3]([NH:5][C:6]1[N:10]([CH2:11][CH3:12])[N:9]=[C:8]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:7]=1)=[O:4].C(O)C.Br[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]>C(N(CC)CC)C>[CH2:11]([N:10]1[C:6]([NH:5][C:3](=[O:4])[C@@H:2]([NH:1][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:7][C:8]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:9]1)[CH3:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 7748Ethyl bromoacetateHCID 67497598HCID 67497598, compound

Product 1

HCID 67497272HCID 67497272, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To a 25 ml flask was added (S)-2-amino-N-(1-ethyl-3-(pyridin-4-yl)-1H-pyrazol-5-yl)-3-phenylpropanamide 101.1.B (132 mg, 0.39 mmole), 3 ml of ethanol and 0.08 ml of triethylamine. The reaction mixture was cooled to 0° C., and then ethyl bromoacetate (48 μl, 0.43 mmole) was added to the mixture. The reaction was stirred at 50° C. for 1 hour and at room temperature overnight. After then, the solution was concentrated, and dissolved in ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. After concentration in vacuo, the residue was chromatographed on silica gel to give 101.1.C (45 mg, 27% yield) as colorless amorphous. 1H NMR (400 MHz, CDCl3) δ ppm 9.73 (s, 1H), 8.61 (d, J=5.9 Hz, 2H), 7.69 (d, J=6.3 Hz, 2H), 7.38-7.26 (m, 5H), 6.87 (s, 1H), 4.19-4.04 (m, 4H), 3.54 (dd, J=8.4, 4.5 Hz, 1H), 3.42 (d, J=17.6 Hz, 1H), 3.32 (d, J=17.6 Hz, 1H), 3.35 (dd, J=14.1, 4.5 Hz, 1H), 3.00 (dd, J=14.1, 8.2 Hz, 1H), 2.05 (brs, 1H), 1.43 (t, J=7.2 Hz, 3H), 1.24 (t, J=7.2 Hz, 3H).

Workup

  1. concentrationAfter then, the solution was concentrated
  2. dissolutiondissolved in ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationAfter concentration in vacuo
  6. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-61c00709b74f4dc591872f17aa5af2ce
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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