Hydrochloric Acid → HCID 117778902, 화합물

HRID 1526991노트

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HRID 1526991 반응식
[CH3:1][C:2]1[N:10]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:19]([O:21]C)=[O:20].[OH-].[Li+].Cl>CO.O>[CH3:1][C:2]1[N:10]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:19]([OH:21])=[O:20]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 89740370HCID 89740370, 화합물

생성물 1

HCID 117778902HCID 117778902, 화합물수율 26.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

To a solution of methyl 2-methyl-1-(1-phenylethyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylate (80 mg, 0.27 mmol) in methanol (3 mL) and water (1 mL) was added lithium hydroxide (57 mg, 1.36 mmol). The reaction mixture was stirred with refluxing for 15 hours. The mixture was adjusted pH 3 with 1N aqueous hydrochloric acid. The aqueous phase was extracted with dichloromethane (50 mL×3). The organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give a residue, which was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give 2-methyl-1-(1-phenylethyl)-1H-pyrrolo-[3,2-b]pyridine-3-carboxylic acid (20 mg, 26%). LRMS (M−H+) m/z: calcd 279.12. found 279.

후처리

  1. temperaturewith refluxing for 15 hours
  2. extractionThe aqueous phase was extracted with dichloromethane (50 mL×3)
  3. washThe organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue, which
  8. customwas purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

출처 및 근거

ORD 기록
ord-dfa89d70a1fb4e949e1d0a15d4a85247
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085583B2

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