Hydrochloric Acid → HCID 67496846, compound

HRID 1628338Notes

Reaction equation

[CH2:1]([N:3]1[C:7]([NH:8][C:9](=[O:25])[C@@H:10]([NH:18][CH2:19][C:20]([O:22]CC)=[O:21])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[N:4]1)[CH3:2].[OH-].[Na+].Cl>CO>[CH2:1]([N:3]1[C:7]([NH:8][C:9](=[O:25])[C@@H:10]([NH:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][C:5]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[N:4]1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a 25 ml flask was added ethyl 2-((S)-1-(1-ethyl-3-(pyridin-4-yl)-1H-pyrazol-5-ylamino)-1-oxo-3-phenylpropan-2-ylamino)acetate 101.1.C (105 mg, 0.78 mmole), 0.5 ml of 1N-sodium hydroxide solution and 1.5 ml of methanol. The mixture was stirred at room temperature for 1 hour and at 50° C. for 1 hour. After then, 0.25 ml of 2N-hydrogen chloride solution was added to neutralize. The solvent was removed by rotary evaporation. The crude product was purified by silica gel chromatography to give 101.2 (79 mg, 81% yield) as colorless powder. LCMS ESI (pos.) m/e: 394 (M+H); 1H NMR (400 MHz, DMSO-d6) δ ppm 8.57 (d, J=5.9 Hz, 2H), 7.72 (d, J=5.8 Hz, 2H), 7.34-7.22 (m, 5H), 6.79 (s, 1H), 3.89 (q, J=7.4 Hz, 2H), 3.66 (t, J=7.1 Hz, 1H), 3.30 (d, J=17.2 Hz, 1H), 3.24 (d, J=17.2 Hz, 1H), 3.04-2.93 (m, 2H), 1.24 (t, J=7.2 Hz, 3H).

Workup

customThe solvent was removed by rotary evaporation
customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record: ord-9491e91905454523a9ad4fb076ec944e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785468B2

Reaction notes

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