Hydrochloric Acid → HCID 68817755, compound

HRID 736768Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-acetyl-4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-piperidine-4-carboxylic acid ethyl ester (0.4 g, 7.6 mmol) in 1,4-dioxane (4 mL) was added concentrated HCl (4 mL). The reaction was heated to 60° C. for 19 h. The solvent was then removed in vacuo and 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)-benzenesulfonyl amino]-piperidine-4-carboxylic acid as an amorphous white solid (0.2 g, 63.1%). MS: 498 (M+H)+.

Workup

customThe solvent was then removed in vacuo
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-a26df9ee0cce44b6a0ca70f9320d60a3
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595327B2

Reaction notes

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