Hydrochloric Acid → HCID 11235229, compound

HRID 1726461Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

4-(4-Benzoylamino-naphthalene-1-sulfonylamino)-piperidine-1-carboxylic acid tert-butyl ester (11) was prepared following the general procedure in Scheme 2. To a solution of 4-(4-benzoylamino-naphthalene-1-sulfonylamino)-piperidine-1-carboxylic acid tert-butyl ester (11) in MeOH was added a solution of 4 N HCl in dioxane. The reaction mixture was stirred at 25° C. for 5 h and then concentrated in vacuo. The crude material was purified by reverse phase HPLC to provide the title compound. 1H NMR (300 MHz, MeOH) δ 8.75 (d, 1H), 8.46 (s, 1H), 8.33 (d, 1H), 8.21 (d, 1H), 8.10 (m, 1H), 8.07 (m, 1H), 7.83 (d, 1H), 7.69 (m, 5H), 3.21 (m, 3H), 2.92 (m, 2H), 1.82 (m, 2H), 1.60 (m, 2H); LC/MS (M+H)+ m/z 410.

Workup

concentrationconcentrated in vacuo
customThe crude material was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-ac68c206550f46a0bfcd052e3231ed62
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491827B2

Reaction notes

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