Methyl N-(triethylammoniosulfonyl)carbamate → 5-[5-(4-Allyloxy-3,5-dimethyl-phenyl)-[1,3,4]oxadiazol-2-yl]-2-isobutyl-3-methyl-pyridine

HRID 2065919노트

반응식

HRID 2065919 반응식
[CH2:1]([O:4][C:5]1[C:27]([CH3:28])=[CH:26][C:8]([C:9]([NH:11][NH:12][C:13](=O)[C:14]2[CH:19]=[C:18]([CH3:20])[C:17]([CH2:21][CH:22]([CH3:24])[CH3:23])=[N:16][CH:15]=2)=[O:10])=[CH:7][C:6]=1[CH3:29])[CH:2]=[CH2:3].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1.CC(=O)OCC>[CH2:1]([O:4][C:5]1[C:27]([CH3:28])=[CH:26][C:8]([C:9]2[O:10][C:13]([C:14]3[CH:19]=[C:18]([CH3:20])[C:17]([CH2:21][CH:22]([CH3:23])[CH3:24])=[N:16][CH:15]=3)=[N:12][N:11]=2)=[CH:7][C:6]=1[CH3:29])[CH:2]=[CH2:3]

참가 물질

5

반응물 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 687652896-isobutyl-5-methyl-nicotinic acid N'-(4-allyloxy-3,5-dimethyl-benzoyl)-hydrazide

생성물 1

HCID 687661605-[5-(4-Allyloxy-3,5-dimethyl-phenyl)-[1,3,4]oxadiazol-2-yl]-2-isobutyl-3-methyl-pyridine수율 94.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 6-isobutyl-5-methyl-nicotinic acid N′-(4-allyloxy-3,5-dimethyl-benzoyl)-hydrazide (89 mg, 0.224 mmol) and Burgess reagent (162 mg, 0.68 mmol) in THF (4 mL) is heated in a microwave oven at 110° C. for 6 min. The mixture is diluted with EA (15 mL) and washed with 1M aq. NaH2PO4 (5 mL), 1M aq. NaOH (5 mL) and water (5 mL). The org. phase is dried (MgSO4), filtered and evaporated to provide crude 5-[5-(4-allyloxy-3,5-dimethyl-phenyl)-[1,3,4]oxadiazol-2-yl]-2-isobutyl-3-methyl-pyridine (80 mg); LC-MS: tR=1.07 min, [M+1]+=378.3.

후처리

  1. washwashed with 1M aq. NaH2PO4 (5 mL), 1M aq. NaOH (5 mL) and water (5 mL)
  2. dry with materialphase is dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

출처 및 근거

ORD 기록
ord-c396a6b414cc444eb45d04b282d1d83e
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288554B2

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