Ethyl Acetate → HCID 178521722, compound

HRID 1276295Notes

Reaction equation

HRID 1276295 reaction equation
N[C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[NH:4][N:3]=1.Cl.[C:15]1([N:21]2[CH2:26][CH2:25][CH:24](C(O)=O)[CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.C[N:32]([CH3:41])CCCN=C=NCC.C(OCC)(=[O:44])C>N1C=CC=CC=1>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[NH:4][N:3]=[C:2]([CH:24]3[CH2:23][CH2:22][N:21]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:26][CH2:25]3)[C:6]=2[N:32]=[C:41]=[O:44])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27353053-(4-chlorophenyl)-1H-pyrazol-5-amineHCID 699487101-Phenylpiperidine-4-carboxylic acid--hydrogen chloride (1/1)

Product 1

HCID 178521722HCID 178521722, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Amino-5-(4-chlorophenyl)pyrazole (23 mg) and 1-phenylpiperidine-4-carboxylic acid hydrochloride (28 mg) were dissolved in pyridine (5 ml) to which was subsequently added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (35 mg), and the mixture was stirred overnight at room temperature. The reaction solution was diluted with ethyl acetate (30 ml), washed with water (30 ml), saturated aqueous sodium bicarbonate (30 ml) and saturated brine (30 ml) and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled away. The resulting residue was crystallized from ethyl ether to obtain the title compound (20 mg) as white crystals (melting point: 209-211° C.).

Workup

  1. washwashed with water (30 ml), saturated aqueous sodium bicarbonate (30 ml) and saturated brine (30 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThen, the solvent was distilled away
  4. customThe resulting residue was crystallized from ethyl ether

Sources & evidence

ORD record
ord-323bcefee8084df3bc64c09ed1fd1708
Source dataset
uspto-grants-2000_12
Patent number
US06166038

Reaction notes

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