Methyl N-(triethylammoniosulfonyl)carbamate → 2-Isobutyl-4-[2-(2,6-dimethyl-4-pyridinyl)-oxazol-5-yl]-6-methyl-pyridine

HRID 1908865Notes

Reaction equation

[CH2:1]([C:5]1[CH:10]=[C:9]([C:11](=[O:24])[CH2:12][NH:13][C:14](=O)[C:15]2[CH:20]=[C:19]([CH3:21])[N:18]=[C:17]([CH3:22])[CH:16]=2)[CH:8]=[C:7]([CH3:25])[N:6]=1)[CH:2]([CH3:4])[CH3:3].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[CH2:1]([C:5]1[CH:10]=[C:9]([C:11]2[O:24][C:14]([C:15]3[CH:20]=[C:19]([CH3:21])[N:18]=[C:17]([CH3:22])[CH:16]=3)=[N:13][CH:12]=2)[CH:8]=[C:7]([CH3:25])[N:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-[2-(2-isobutyl-6-methyl-pyridin-4-yl)-2-oxo-ethyl]-2,6-dimethyl-isonicotinamide (9 mg, 27 μmol) in THF (1 mL), Burgess reagent (20 mg, 80 μmol) is added. The mixture is stirred at 60° C. for 2 h before it is concentrated. The crude product is purified on prep. TLC plates with DCM containing 5% of methanol to give 2-isobutyl-4-[2-(2,6-dimethyl-4-pyridinyl)-oxazol-5-yl]-6-methyl-pyridine (5 mg) as a pale yellow wax; LC-MS: tR=0.96*, [M+1]+=322.12; 1H NMR (CDCl3): δ 1.00 (d, J=6.8 Hz, 6H), 2.13-2.24 (m, 1H), 2.64 (s, 3H), 2.66 (s, 6H), 2.72 (d, J=7.3 Hz, 2H), 7.24 (s, 1H), 7.31 (s, 1H), 7.67 (s, 3H).

Workup

concentrationis concentrated
customThe crude product is purified on prep

Sources & evidence

ORD record: ord-4e5dc700c968457b95e281c19305f3ae
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598208B2

Reaction notes

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