Hydrochloric Acid → HCID 68817249, compound

HRID 736758Notes

Reaction equation

C([O:3][C:4]([CH:6]1[CH:11]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=[C:26]([CH3:34])[CH:25]=3)=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:10][CH2:9][N:8]([C:35](=[O:37])[CH3:36])[CH2:7]1)=[O:5])C.Cl>O1CCOCC1>[C:35]([N:8]1[CH2:9][CH2:10][CH:11]([NH:12][S:13]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=[C:26]([CH3:34])[CH:25]=3)=[CH:20][CH:21]=2)(=[O:15])=[O:14])[CH:6]([C:4]([OH:5])=[O:3])[CH2:7]1)(=[O:37])[CH3:36]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-acetyl-4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-3-carboxylic acid ethyl ester (0.6 g, 1.14 mmol) in 1,4-dioxane (10 mL) was added concentrated HCl (10 mL). The reaction was heated at 60° C. for 19 h. The solvent was removed in vacuo and the residue was diluted with CH2Cl2. The organics were dried over MgSO4, filtered and concentrated. The residue was purified by reverse phase HPLC (Gilson) on a Phenomex C-18 semi-prep column eluting an acetonitrile:water gradient, to afford 1-acetyl-4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-3-carboxylic acid as an amorphous white solid (0.4 g, 70.1%). MS: 498 (M+H)+.

Workup

customThe solvent was removed in vacuo
additionthe residue was diluted with CH2Cl2
dry with materialThe organics were dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by reverse phase HPLC (Gilson) on a Phenomex C-18 semi-prep column
washeluting an acetonitrile

Sources & evidence

ORD record: ord-9fa5db2f21424787a8bcf879bfee5272
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595327B2

Reaction notes

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