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

HRID 1472544
Notes
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Reaction equation

HRID 1472544 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59314454N-{1-Ethyl-3-[2-oxo-2(1-pyrrolidinyl)ethyl]-1H-pyrazol-5-yl}-2,2,2-trifluoroacetamide

Product 1

HCID 575169011-ethyl-3-[2-oxo-2-(1-pyrrolidinyl)ethyl]-1H-pyrazol-5-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. concentrationconcentrated
  2. concentrationconcentrated
  3. customThe residue was dried under high vacuum
  4. customto give 79 mg
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes