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

HRID 2065919ノート

反応式

HRID 2065919 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c396a6b414cc444eb45d04b282d1d83e
出典データセット
uspto-grants-2012_10
特許番号
US08288554B2

反応ノート

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