Ammonia methanol → 4-[(6-Chloro-2-naphthyl)sulfonyl)-1-[methyl[1-(4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazinecarboxamide Hydrochloride

HRID 2086305Notes

Reaction equation

HRID 2086305 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][C:20](=[O:22])[N:19]([N:23]([CH3:36])[CH:24]3[CH2:29][CH2:28][N:27]([C:30]4[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=4)[CH2:26][CH2:25]3)[CH:18]([C:37](OC)=[O:38])[CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2.[NH3:41].CO>>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][C:20](=[O:22])[N:19]([N:23]([CH3:36])[CH:24]3[CH2:25][CH2:26][N:27]([C:30]4[CH:31]=[CH:32][N:33]=[CH:34][CH:35]=4)[CH2:28][CH2:29]3)[CH:18]([C:37]([NH2:41])=[O:38])[CH2:17]1)(=[O:14])=[O:15])[CH:7]=[CH:6]2

Participants

3

Reactant 2

HCID 21705897Ammonia methanolHCID 22727077Methyl 4-[(6-chloro-2-naphthyl)sulfonyl)-1-[methyl[1-(4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazinecarboxylate hydrochloride

Product 1

HCID 227270584-[(6-Chloro-2-naphthyl)sulfonyl)-1-[methyl[1-(4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazinecarboxamide Hydrochloride

Procedure

Methyl 4-[(6-chloro-2-naphthyl)sulfonyl)-1-[methyl[1-(4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazinecarboxylate hydrochloride (0.3 g) obtained in Example 54 and 13% ammonia/methanol solution (3.5 ml) were heated in a sealed tube at 90° C. for 2 days. The reaction system was cooled, and concentrated under reduced pressure. The residue was purified on a CHP-20 column (water→1% 1N hydrochloric acid-containing 30% aqueous solution of acetonitrile) to obtain the title compound (0.11 g) as a colorless powder.

Workup

  1. temperatureThe reaction system was cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified on a CHP-20 column (water→1% 1N hydrochloric acid-containing 30% aqueous solution of acetonitrile)

Sources & evidence

ORD record
ord-d13ca05a1a684674aeadc2382398401d
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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