Hydrochloric Acid → HCID 131714542, compound

HRID 482876Notes

Reaction equation

HRID 482876 reaction equation
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=3)[CH2:11][CH2:10]2)[NH:4][N:3]=1.CN(C)[CH:26]=[CH:27][C:28]([C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)=O.[ClH:37]>C(O)(=O)C.C(O)(C)C>[ClH:37].[CH3:23][O:22][C:18]1[CH:17]=[C:16]([CH2:15][N:12]2[CH2:13][CH2:14][N:9]([C:5]3[C:6]([C:7]#[N:8])=[C:2]4[N:1]=[CH:26][CH:27]=[C:28]([C:30]5[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=5)[N:3]4[N:4]=3)[CH2:10][CH2:11]2)[CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-oneHCID 178490265HCID 178490265, compound

Product 1

HCID 131714542HCID 131714542, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of 5.0 g of 3-amino-5-[4-[(3-methoxyphenyl)methyl]-1-piperazinyl]-1H-pyrazole-4-carbonitrile (prepared as described in Example 19) and 2.9 g of 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one (U.S. Pat. No. 4,281,000, Example 1) in 25 ml of glacial acetic acid was heated at reflux for 3 hours. The work procedure of Example 21 was followed to obtain a gummy solid. The solid was dissolved in isopropanol and was treated with 20 ml of 2.9N ethanolic hydrochloric acid. The yellow precipitate formed was collected by filtration, washed with isopropanol and dried in vacuo. The product was recrystallized from ethanol/water and gave 2.5 g of the desired product as a yellow solid, mp >250° C.

Workup

  1. temperatureat reflux for 3 hours
  2. customto obtain a gummy solid
  3. customThe yellow precipitate formed
  4. filtrationwas collected by filtration
  5. washwashed with isopropanol
  6. customdried in vacuo
  7. customThe product was recrystallized from ethanol/water

Sources & evidence

ORD record
ord-d7c9abddb4294b39972537c8bcb52743
Source dataset
uspto-grants-1986_03
Patent number
US04576943

Reaction notes

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