1-Aminopiperidine → HCID 86643691, compound

HRID 1504580Notes

Reaction equation

HRID 1504580 reaction equation
[N:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([C:11]1[N:12]=[C:13]([CH:16]2[CH2:21][CH2:20][N:19]([C:22](=[O:34])[CH2:23][N:24]3[C:28]([CH3:29])=[CH:27][C:26]([C:30]([F:33])([F:32])[F:31])=[N:25]3)[CH2:18][CH2:17]2)[S:14][CH:15]=1)(=O)[CH3:9]>[Cl-].[NH4+]>[CH3:29][C:28]1[N:24]([CH2:23][C:22]([N:19]2[CH2:20][CH2:21][CH:16]([C:13]3[S:14][CH:15]=[C:11]([C:8](=[N:7][N:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)[CH3:9])[N:12]=3)[CH2:17][CH2:18]2)=[O:34])[N:25]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:27]=1

Participants

4

Reactant 2

HCID 166581-AminopiperidineHCID 67433897HCID 67433897, compound

Product 1

HCID 86643691HCID 86643691, compound

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

At 80° C., piperidine-1-amine (104 mg) is added to a solution of 1-[4-(4-acetyl-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (46 mg). The reaction mixture is stirred at this temperature for a further 2 hours. Aqueous ammonium chloride solution (10 ml) is then added to the reaction mixture. After phase separation, the aqueous phase is extracted three times with methyl tert-butyl ether (20 ml). All the organic phases are dried over Na2SO4. The mixture is then filtered and concentrated under reduced pressure. This gives 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[N-(piperidin-1-yl)ethanimidoyl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone (55 mg, 99%), (log P (pH2.7)=3.69).

Workup

  1. customAfter phase separation
  2. extractionthe aqueous phase is extracted three times with methyl tert-butyl ether (20 ml)
  3. dry with materialAll the organic phases are dried over Na2SO4
  4. filtrationThe mixture is then filtered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d44f758433514ddfa392e404d7057139
Source dataset
uspto-grants-2015_12
Patent number
US09215875B2

Reaction notes

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