Diisopropylethylamine → HCID 136170273, 화합물

HRID 2065914노트

반응식

HRID 2065914 반응식
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]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67027015HCID 67027015, 화합물HCID 178436626HCID 178436626, 화합물

생성물 1

HCID 136170273HCID 136170273, 화합물수율 28.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-76625bef59204222b60b49a4028b7406
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288554B2

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