Hydrochloric Acid → 1-ethyl-3-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1H-pyrazol-5-amine

HRID 1472544Notes

Reaction equation

[CH2:1]([N:3]1[C:7]([NH:8]C(=O)C(F)(F)F)=[CH:6][C:5]([CH2:15][C:16](=[O:22])[N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:4]1)[CH3:2].Cl>CO>[CH2:1]([N:3]1[C:7]([NH2:8])=[CH:6][C:5]([CH2:15][C:16](=[O:22])[N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)=[N:4]1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of N-{1-ethyl-3-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1H-pyrazol-5-yl}-2,2,2-trifluoroacetamide (120 mg, 0.377 mmol) in methanol (1.5 mL) was added 2M HCl (1 mL, 0.377 mmol), and the reaction mixture was stirred at 50° C. for 2 h and concentrated. The residue was neutralized using saturated NaHCO3 solution and concentrated. The residue was dried under high vacuum to give 79 mg and used for next reaction without further purification. MS: (M+H)+=222.8. 1H NMR (400 MHz, DMSO-d6) ppm 1.18 (t, J=7.2 Hz, 3H), 1.70-1.85 (m, 4 H), 3.24 (t, J=6.8 Hz, 2H), 3.31 (s, 2 H), 3.43 (t, J=6.8 Hz, 2H), 3.78 (q, J=7.2 Hz, 2H), 5.11 (s, 1H).

Workup

concentrationconcentrated
concentrationconcentrated
customThe residue was dried under high vacuum
customto give 79 mg
customused for next reaction without further purification

Sources & evidence

ORD record: ord-bd64c682bc184a638d533295ea5cf7e5
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012479B2

Reaction notes

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