Hydrochloric Acid → HCID 131723414, compound

HRID 489956Notes

Reaction equation

HRID 489956 reaction equation
[ClH:1].[C:2]([Cl:5])(=[O:4])[CH3:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:16]([N:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]3)[NH:15][N:14]=2)=[CH:9][CH:8]=1.[CH3:37]O>>[OH2:4].[ClH:5].[ClH:6].[ClH:1].[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]([CH2:37][C:2]#[CH:3])[N:15]=[C:16]([N:24]3[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]3)[C:17]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 6367Acetyl chlorideHCID 178452276HCID 178452276, compound

Product 1

HCID 131723414HCID 131723414, compoundYield 90%

Conditions

Temperature
5 °C

Procedure

A solution of HCl in methanol (5 mL) was generated by addition of acetyl chloride (200 mg) to methanol while cooling (5° C.). 3-(4-Chlorophenyl)-4-(4-pyridyl)-5-(4-N-tert.-butoxycarbonylpiperazinyl)pyrazole (100 mg, 0.2 mmol) prepared above was added and the reaction stirred in the cold for one hour. The reaction mixture was concentrated in vacuo and the residue azeotroped with toluene to give 100 mg of 1-[5-(4-chlorophenyl)-4-(4-pyridinyl)-1-(2-propynyl)-1H-pyrazol-3-yl]piperazine, trihydrochloride monohydrate (90%), m.p.=231-233° C. (dec.). Anal. Calc'd. for C21H20N5Cl.3HCl.H2O: C, 49.92; H, 4.99; N, 13.86. Found: C, 49.71; H, 4.89; N, 13.61.

Workup

  1. additionabove was added
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue azeotroped with toluene

Sources & evidence

ORD record
ord-48ebdb9d32fb4e78940d99bd558ae630
Source dataset
uspto-grants-2005_12
Patent number
US06979686B1

Reaction notes

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