1-Hydroxybenzotriazole → HCID 66618584, compound

HRID 1661171Notes

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 7H. 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-702b3d96cde14f8489d32426ff0a62d3
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030331B2

Reaction notes

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