Acetic Acid → 1H-Pyrazole-3-carboxamide, 4-[(2,6-dichlorobenzoyl)amino]-N-4-piperidinyl-, acetate (1:1)

HRID 907453Notes

Reaction equation

HRID 907453 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[C:14]([NH:15][C:16](=[O:25])[C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:24])=[CH:13][NH:12][N:11]=2)=[O:9])[CH2:3][CH2:2]1.[C:26]([OH:29])(=[O:28])[CH3:27]>CO>[C:26]([OH:29])(=[O:28])[CH3:27].[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[C:14]([NH:15][C:16](=[O:25])[C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:24])=[CH:13][NH:12][N:11]=2)=[O:9])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 178522298HCID 178522298, compound

Product 1

HCID 1784767371H-Pyrazole-3-carboxamide, 4-[(2,6-dichlorobenzoyl)amino]-N-4-piperidinyl-, acetate (1:1)Yield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 4-(2,6-dichloro-benzoylamino)-1H-pyrazole-3-carboxylic acid piperidin-4-ylamide (10.0 g, 26.2 mmol) in methanol (150 ml) was added glacial acetic acid (15 ml, 262 mmol) at ambient temperature. After 1 h, a clear solution was obtained which was reduced in vacuo azeotroping with toluene (×2). The residue was then triturated with acetonitrile (2×100 ml) and the solid dried in vacuo to give 4-(2,6-dichloro-benzoylamino)-1H-pyrazole-3-carboxylic acid piperidin-4-ylamide acetic acid salt (10.3 g) as a white solid.

Workup

  1. customa clear solution was obtained which
  2. customazeotroping with toluene (×2)
  3. customThe residue was then triturated with acetonitrile (2×100 ml)
  4. customthe solid dried in vacuo

Sources & evidence

ORD record
ord-c699b85b8a5e461e8478b3c3efebf05c
Source dataset
uspto-grants-2011_09
Patent number
US08013163B2

Reaction notes

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