Ethylorthoformate → Bis-(3-methyl-pyridin-2-ylmethyl)-(1-[1,2,4]oxadiazol-3-yl-piperidine-4-yl)-amine

HRID 1592595Notes

Reaction equation

[CH3:1][C:2]1[C:3]([CH2:8][N:9]([CH2:20][C:21]2[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][N:22]=2)[CH:10]2[CH2:15][CH2:14][N:13]([C:16]([NH:18][OH:19])=[NH:17])[CH2:12][CH2:11]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:28]([O-])([O-])OCC>O1CCOCC1>[CH3:1][C:2]1[C:3]([CH2:8][N:9]([CH2:20][C:21]2[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][N:22]=2)[CH:10]2[CH2:11][CH2:12][N:13]([C:16]3[N:17]=[CH:28][O:19][N:18]=3)[CH2:14][CH2:15]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-[bis-(3-methyl-pyridin-2-ylmethyl)-amino]-N-hydroxy-piperidine-1-carboxamidine (50 mg, 0.13 mmol), dioxane (2 ml) and ethyl orthoformate (2 ml) were heated for 17 hours at 100° C. The volatiles were removed in vaccuo, and the residue was purified using radial chromatography on silica gel (20:1:1 CH2Cl2:MeOH:NH4OH) to provide COMPOUND 335 as a yellow oil (34.2 mg, 69%). 1H NMR (CHCl3) δ 1.70-1.82 (m, 5H), 1.96-2.00 (m, 2H), 2.10 (s, 6H), 2.68-2.86 (m, 3H), 3.83 (s, 4H), 4.08-4.13 (m, 2H), 7.09 (dd, 2H, J=5.7, 8.4 Hz), 7.37 (d, 2H, J=8.4 Hz), 8.29 (s, 1H), 8.34 (d, 2H, J=5.7 Hz); 13C NMR (CHCl3) δ 18.4, 26.7, 46.9, 55.0, 57.6, 122.8, 133.8, 138.4, 146.3, 157.6, 164.3, 169.9; ES-MS m/z 401 (M+Na). Anal. Calcd. for C21H26N6.0.2H2O.0.4CH2Cl2: C, 61.78; H, 6.59; N, 20.20. Found: C, 61.77; H, 6.59; N, 19.93.

Workup

customThe volatiles were removed in vaccuo
customthe residue was purified

Sources & evidence

ORD record: ord-122da1626f764600bd6aa031fbae0d0d
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291631B2

Reaction notes

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