Diisopropylethylamine → HCID 136170273、化合物

HRID 2065914ノート

反応式

HRID 2065914 の反応式
Cl.[CH2:2]([C:4]1[C:5]([CH2:13][CH3:14])=[N:6][CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=O)[CH3:3].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:46]([C:48]1[CH:49]=[C:50]([CH:55]=[C:56]([CH3:59])[C:57]=1[OH:58])[C:51]([NH:53]O)=[NH:52])[CH3:47]>C(Cl)Cl>[CH2:2]([C:4]1[CH:12]=[C:8]([C:9]2[O:11][N:53]=[C:51]([C:50]3[CH:55]=[C:56]([CH3:59])[C:57]([OH:58])=[C:48]([CH2:46][CH3:47])[CH:49]=3)[N:52]=2)[CH:7]=[N:6][C:5]=1[CH2:13][CH3:14])[CH3:3]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67027015HCID 67027015、化合物HCID 178436626HCID 178436626、化合物

生成物 1

HCID 136170273HCID 136170273、化合物収率 28.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 5,6-diethyl-nicotinic acid hydrochloride (920 mg, 4.3 mmol) and Hünig's base (2.76 g, 21 mmol) in DCM (50 mL) is added TBTU (1.785 g, 5.55 mmol) and the mixture is stirred at rt for 5 min. 3-Ethyl-4,N-dihydroxy-5-methyl-benzamidine (1.14 g, 4.7 mmol) is added and the mixture stirred for 0.5 h. The mixture is diluted with DCM, washed with sat. aq. NaHCO3 solution, dried over MgSO4, filtered and concentrated. The crude 5,6-diethyl-nicotinic acid (3-ethyl-4,N-dihydroxy-5-methyl-benzamidine) ester (LC-MS: tR=0.79 min) is dissolved in dioxane (50 mL) and heated to 100° C. for 18 h. The solvent is evaporated and the crude product is purified by FC on silica gel eluting with heptane:EA 10:1 to give 4-[5-(5,6-diethyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenol (0.42 g) as a solid; LC-MS: tR=1.03 min, [M+1]+=338.09.

後処理

  1. stirringthe mixture stirred for 0.5 h
  2. washwashed with sat. aq. NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe crude 5,6-diethyl-nicotinic acid (3-ethyl-4,N-dihydroxy-5-methyl-benzamidine) ester (LC-MS: tR=0.79 min) is dissolved in dioxane (50 mL)
  7. temperatureheated to 100° C. for 18 h
  8. customThe solvent is evaporated
  9. customthe crude product is purified by FC on silica gel eluting with heptane:EA 10:1

出典と根拠

ORDレコード
ord-76625bef59204222b60b49a4028b7406
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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