Hydrochloric Acid → HCID 178474531, 화합물

HRID 554647노트

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HRID 554647 반응식
C1CCCCC=1.O1CCCC1.B.[CH2:13]([N:20]([CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[C:35]1[C:36]([O:43]C)=[N:37][CH:38]=[C:39]([C:41]#[CH:42])[CH:40]=1)[C:21](=[O:23])[CH3:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-:45].[Na+].[OH:47]O.Cl>C1COCC1.CO>[C:21]([N:20]([CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:28]=[CH:27][C:26]=1[C:35]1[CH:40]=[C:39]([CH2:41][C:42]([OH:47])=[O:45])[CH:38]=[N:37][C:36]=1[OH:43])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:23])[CH3:22]

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 8079CyclohexeneHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 86640542N-Benzyl-N-[2-(5-ethynyl-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide

생성물 1

HCID 178474531HCID 178474531, 화합물

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To cyclohexene (0.20 mL, 1.98 mmol) at room temperature was added borane tetrahydrofuran complex (1M in THF; 1.01 mL, 1.01 mmol), and the reaction was stirred for 45 minutes. N-Benzyl-N-[2-(5-ethynyl-2-methoxy-pyridin-3-yl)-5-trifluoromethyl-benzyl]-acetamide (0.126 g, 0.29 mmol) in THF (2 mL) was added dropwise, and the reaction was stirred for 2 hours at room temperature. The mixture was cooled to 0° C., and MeOH (1 mL) and 1N aqueous NaOH (1.01 mL, 1.01 mmol) were added, followed by hydrogen peroxide (30%; 0.31 mL, 3.00 mmol), and the reaction was stirred for 1 hour at 0° C. The mixture was acidified with 1N aqueous HCl and extracted with EtOAc, and the combined organic layers were dried, filtered, and concentrated. The residue was purified by preparative HPLC to give (5-{2-[(N-Acetyl-N-benzyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-hydroxy-pyridin-3-yl)-acetic acid.

후처리

  1. stirringthe reaction was stirred for 2 hours at room temperature
  2. stirringthe reaction was stirred for 1 hour at 0° C
  3. extractionextracted with EtOAc
  4. customthe combined organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-b64b1b78bde446c1a970ae2f4fd9107a
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08049015B2

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