Ethanol, reaction products with ammonia, distn. residues → HCID 22727227, compound

HRID 2086318Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][C:19](=[O:21])[N:18]([NH:22][CH:23]3[CH2:28][CH2:27][N:26]([C:29]4[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[CH:30]=4)[CH2:25][CH2:24]3)[CH:17]([CH2:36][C:37]([O:39]C)=O)[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[NH3:41].C(O)C>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][C:19](=[O:21])[N:18]([NH:22][CH:23]3[CH2:28][CH2:27][N:26]([C:29]4[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[CH:30]=4)[CH2:25][CH2:24]3)[CH:17]([CH2:36][C:37]([NH2:41])=[O:39])[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2

Participants

Reactant 2

HCID 22020343Ethanol, reaction products with ammonia, distn. residues

HCID 69545679HCID 69545679, compound

Product 1

HCID 22727227HCID 22727227, compound

Procedure

Methyl 4-[(6-chloro-2-naphthyl)sulfonyl]-1-[[1-(2-methyl-4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazineacetate (100 mg) obtained in Example 138 and a 13% ammonia/ethanol solution (6.0 ml) were heated in a sealed tube at 90° C. for 6 hours. The reaction mixture was cooled and concentrated under reduced pressure. The residue obtained was purified by a column chromatography on a silica gel (dichloromethane: 10% aqueous ammonia-containing methanol=15:1) and crystallized from a mixture of ethyl acetate and diethyl ether to obtain the title compound (12 mg) as colorless crystals.

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated under reduced pressure
customThe residue obtained
customwas purified by a column chromatography on a silica gel (dichloromethane: 10% aqueous ammonia-containing methanol=15:1)
customcrystallized from a mixture of ethyl acetate and diethyl ether

Sources & evidence

ORD record: ord-5755d5c2473b4002b183f75a568b56f2
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06723722B1

Reaction notes

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