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Water → 2-Amino-6-{[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methoxy}-4-[4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile

HRID 2092261
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HRID 2092261 반응식
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][CH:16]=[C:17]([CH2:19][OH:20])[N:18]=2)=[CH:10][CH:9]=1.[NH2:21][C:22]1[C:27]([C:28]#[N:29])=[C:26]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][OH:39])=[CH:32][CH:31]=2)[C:25]([C:40]#[N:41])=[C:24](SC2C=CC=CC=2)[N:23]=1.O>COCCOC.C(O)(=O)C>[NH2:21][C:22]1[C:27]([C:28]#[N:29])=[C:26]([C:30]2[CH:31]=[CH:32][C:33]([O:36][CH2:37][CH2:38][OH:39])=[CH:34][CH:35]=2)[C:25]([C:40]#[N:41])=[C:24]([O:20][CH2:19][C:17]2[N:18]=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][CH:12]=3)[O:15][CH:16]=2)[N:23]=1
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참가 물질

7

반응물 4

HCID 962WaterHCID 15555159HCID 15555159, 화합물HCID 23665647Potassium tert-butoxideHCID 666304992-Amino-4-[4-(2-hydroxyethoxy)phenyl]-6-phenylthiopyridine-3,5-dicarbonitrile

생성물 1

HCID 666721372-Amino-6-{[2-(4-chlorophenyl)-1,3-oxazol-4-yl]methoxy}-4-[4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile

시약·촉매·용매 2

HCID 176
Acetic Acid
용매
HCID 80711,2-Dimethoxyethane용매

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온도
60 °C

실험 절차

72 mg (0.64 mmol) of potassium tert-butoxide are suspended in 1 ml of dry 1,2-dimethoxyethane. In succession, 270 mg (1.29 mmol) of the compound from Example 100A and 50 mg (0.13 mmol) of the compound from Example 99A are then added. The reaction mixture is stirred at 60° C. for 2 h and then cooled to RT and stirred at this temperature for a further 8 h. 5 ml of water and 1 ml of 2 N acetic acid are then added to the mixture. A precipitate is formed, which is filtered off with suction and purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5). Removal of the solvent on a rotary evaporator gives the product as a yellow solid.

후처리

  1. temperaturecooled to RT
  2. stirringstirred at this temperature for a further 8 h
  3. customA precipitate is formed
  4. filtrationwhich is filtered off with suction
  5. custompurified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)
  6. customRemoval of the solvent
  7. customon a rotary evaporator

출처 및 근거

ORD 기록
ord-c55d9c06480948bb8aa1e6d66c8d961a
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08440700B2

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