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

HRID 1908865
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HRID 1908865 반응식
[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]
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4

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HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 67027016N-[2-(2-isobutyl-6-methyl-pyridin-4-yl)-2-oxo-ethyl]-2,6-dimethyl-isonicotinamide

생성물 1

HCID 584180942-Isobutyl-4-[2-(2,6-dimethyl-4-pyridinyl)-oxazol-5-yl]-6-methyl-pyridine수율 57.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

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).

후처리

  1. concentrationis concentrated
  2. customThe crude product is purified on prep

출처 및 근거

ORD 기록
ord-4e5dc700c968457b95e281c19305f3ae
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08598208B2

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