Hydrochloric Acid → HCID 67497598, compound

HRID 1628335Notes

Reaction equation

HRID 1628335 reaction equation
[CH2:1]([N:3]1[C:7]([NH:8][C:9](=[O:26])[C@@H:10]([NH:18]C(=O)OC(C)(C)C)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]([C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)=[N:4]1)[CH3:2].Cl>O1CCOCC1>[NH2:18][C@@H:10]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:9]([NH:8][C:7]1[N:3]([CH2:1][CH3:2])[N:4]=[C:5]([C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)[CH:6]=1)=[O:26]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70865475HCID 70865475, compound

Product 1

HCID 67497598HCID 67497598, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a 25 ml flask was added tert-butyl (S)-1-(1-ethyl-3-(pyridin-4-yl)-1H-pyrazol-5-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 101.1.A (568 mg, 1.30 mmole), 5 ml of 4N-hydrogen chloride solution in 1,4-dioxane, and 5 ml of 1,4-dioxane. The reaction was stirred at room temperature for 0.5 hours at which time the solvent was removed by rotary evaporation. The residue was suspended in ethyl acetate, and washed successively with saturated sodium bicarbonate, water and brine. The organic layer was dried over anhydrous sodium sulfate, and concentrated in vacuo to give 101.1.B (380 mg, 87% yield) as colorless syrup. 1H NMR (400 MHz, CDCl3) δ ppm 9.71 (s, 1H), 8.61 (d, J=5.8 Hz, 2H), 7.69 (d, J=6.2 Hz, 2H), 7.39-7.26 (m, 5H), 6.88 (s, 1H), 4.07 (q, J=7.2 Hz, 2H), 3.85 (dd, J=8.8, 4.1 Hz, 1H), 3.36 (dd, J=13.8, 4.1 Hz, 1H), 2.93 (dd, J=13.9, 8.8 Hz, 1H), 2.96 (brs, 2H), 1.45 (t, J=7.2 Hz, 3H).

Workup

  1. customwas removed by rotary evaporation
  2. washwashed successively with saturated sodium bicarbonate, water and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ebda48cd5d9f4cc28e51fe352536468d
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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