Sodium Bicarbonate → 1-{1-[2-(4-hydroxy-7-methoxy-2,2-dimethylchroman-8-yl)ethyl]piperidin-4-yl}-N-methyl-1H-indole-6-carboxamide

HRID 494965노트

반응식

HRID 494965 반응식
[CH3:1][O:2][C:3]1[C:12]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:30]([NH:32][CH3:33])=[O:31])[CH:28]=4)[CH:23]=[CH:22]3)[CH2:17][CH2:16]2)=[C:11]2[C:6]([C:7](=[O:36])[CH2:8][C:9]([CH3:35])([CH3:34])[O:10]2)=[CH:5][CH:4]=1.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>CO>[OH:36][CH:7]1[C:6]2[C:11](=[C:12]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([N:21]4[C:29]5[C:24](=[CH:25][CH:26]=[C:27]([C:30]([NH:32][CH3:33])=[O:31])[CH:28]=5)[CH:23]=[CH:22]4)[CH2:17][CH2:16]3)[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[O:10][C:9]([CH3:35])([CH3:34])[CH2:8]1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 11677552E-2110 free base

생성물 1

HCID 576828731-{1-[2-(4-hydroxy-7-methoxy-2,2-dimethylchroman-8-yl)ethyl]piperidin-4-yl}-N-methyl-1H-indole-6-carboxamide수율 83.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

259 mg of 1-(1-(2-(7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl)piperidin-4-yl)-N-methyl-1H-indole-6-carboxamide was dissolved in 5 ml of methanol. Thereafter, 60 mg of sodium borohydride was added to the reaction solution while cooling on ice. The obtained mixture was then stirred at room temperature overnight. Thereafter, a saturated sodium bicarbonate aqueous solution was added to the reaction solution, followed by extraction with methylene chloride. The extract was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate) and then purified by silica gel column chromatography (ethyl acetate-methanol), so as to obtain 216 mg of the subject compound.

후처리

  1. temperaturewhile cooling on ice
  2. extractionfollowed by extraction with methylene chloride
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (ethyl acetate)
  6. custompurified by silica gel column chromatography (ethyl acetate-methanol)

출처 및 근거

ORD 기록
ord-e055be2c2f3045ff914c75cede837b3e
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538123B2

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