1-Hydroxybenzotriazole → HCID 66618584, compound

HRID 1172735Notes

Reaction equation

[OH:1][NH:2][C:3](=[NH:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.[C:13]([N:20]1[CH2:25][CH2:24][CH2:23][CH:22]([C:26](O)=O)[CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>O1CCOCC1>[C:16]([O:15][C:13]([N:20]1[CH2:25][CH2:24][CH2:23][CH:22]([C:26]2[O:1][N:2]=[C:3]([C:4]3[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=3)[N:12]=2)[CH2:21]1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-Hydroxy-4-methoxy-benzamidine (0.20 g, 1.50 mmol), 1-Boc-piperidine-3-carboxylic acid (0.34 g, 1.50 mmol), HOBT (0.23 g, 1.50 mmol) and EDCI.HCl (0.43 g, 2.25 mmol) in dioxane (2.5 ml) was stirred at R.T for 7 H. After this time the mixture was heated at 80° C. overnight with the carousel Radley's. The mixture was concentrated. The organic layer was washed with water, NaOH 1N and water. The organic layer was dried over Na2SO4, filtered and evaporated. The crude product was purified by flash chromatography (DCM/MeOH: 99/1) to afford 0.39 mg (72%) of 3-[3-(4-Methoxy-phenyl)-[1,2,4]oxadiazol-5-yl]-piperidine-1-carboxylic acid tert-butyl ester as white solid.

Workup

concentrationThe mixture was concentrated
washThe organic layer was washed with water, NaOH 1N and water
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
customevaporated
customThe crude product was purified by flash chromatography (DCM/MeOH: 99/1)

Sources & evidence

ORD record: ord-ecd5040f400c4d5db8f6b9cb3b6f4cee
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834035B2

Reaction notes

Loading…