Water → 1'-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,5-triazin-2-yl]-1,4'-bipiperidinyl-3-ol

HRID 2175088노트

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HRID 2175088 반응식
C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]1[N:13]=[CH:12][N:11]=[C:10]([N:14]2[CH2:19][CH2:18][CH:17]([N:20]3[CH2:25][CH2:24][CH2:23][CH:22]([OH:26])[CH2:21]3)[CH2:16][CH2:15]2)[N:9]=1.CC1(C)C(C)(C)OB([C:35]2[CH:44]=[CH:43][C:42]3[C:41]([CH3:46])([CH3:45])[CH2:40][CH2:39][C:38]([CH3:48])([CH3:47])[C:37]=3[CH:36]=2)O1.O>C1(C)C=CC=CC=1.C(O)C.O>[CH3:45][C:41]1([CH3:46])[CH2:40][CH2:39][C:38]([CH3:48])([CH3:47])[C:37]2[CH:36]=[C:35]([C:8]3[N:13]=[CH:12][N:11]=[C:10]([N:14]4[CH2:19][CH2:18][CH:17]([N:20]5[CH2:25][CH2:24][CH2:23][CH:22]([OH:26])[CH2:21]5)[CH2:16][CH2:15]4)[N:9]=3)[CH:44]=[CH:43][C:42]1=2

참가 물질

6

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 112439294,4,5,5-Tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolaneHCID 532524851-[1-(4-Chloro-1,3,5-triazin-2-yl)piperidin-4-yl]piperidin-3-ol

생성물 1

HCID 532504051'-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,5-triazin-2-yl]-1,4'-bipiperidinyl-3-ol

시약·촉매·용매 1

HCID 86587398Ethanol toluene water용매

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온도
90 °C

실험 절차

45 mg (0.42 mmol) of sodium carbonate are added to 50 mg (0.17 mmol) of 1′-(4-chloro-1,3,5-triazin-2-yl)-1,4′-bipiperidinyl-3-ol and 139 mg (0.42 mmol) of 4,4,5,5-tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane in 3.2 ml of toluene/ethanol/water (3.2/3.2/1). The reaction mixture is degassed a number of times, and 19 mg (0.017 mmol) of tetrakis-(triphenylphosphine)palladium(0) are added under nitrogen atmosphere, the mixture is treated in an ultrasound bath for 10 min and subsequently heated at 90° C. for 5 h. Water is added to the reaction mixture, which is then extracted three times with ethyl acetate/ether. The combined organic phases are dried over Na2SO4 and evaporated. The crude product is purified by means of preparative HPLC.

후처리

  1. additionare added under nitrogen atmosphere
  2. additionthe mixture is treated in an ultrasound bath for 10 min
  3. extractionis then extracted three times with ethyl acetate/ether
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. customevaporated
  6. customThe crude product is purified by means of preparative HPLC

출처 및 근거

ORD 기록
ord-13578d4c243e4abc8f1e0d5c41f7dbd9
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062015B2

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