Benzyl Bromide → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [2-(4-benzyloxypiperidin-1-yl)-1-(S)-(4-fluorobenzyl)-2-oxoethyl]amide

HRID 1693462노트

반응식

HRID 1693462 반응식
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C@H:7]([NH:17][C:18]([C:20]2[NH:29][C:23]3=[CH:24][N:25]=[C:26]([Cl:28])[CH:27]=[C:22]3[CH:21]=2)=[O:19])[C:8]([N:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[H-].[Na+]>CN(C=O)C>[CH2:32]([O:16][CH:13]1[CH2:12][CH2:11][N:10]([C:8](=[O:9])[C@@H:7]([NH:17][C:18]([C:20]2[NH:29][C:23]3=[CH:24][N:25]=[C:26]([Cl:28])[CH:27]=[C:22]3[CH:21]=2)=[O:19])[CH2:6][C:5]2[CH:30]=[CH:31][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:15][CH2:14]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 116986775-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(4-fluorobenzyl)-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]amide

생성물 1

HCID 597537585-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [2-(4-benzyloxypiperidin-1-yl)-1-(S)-(4-fluorobenzyl)-2-oxoethyl]amide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(4-fluorobenzyl)-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]amide (EXAMPLE 5, 50 mg, 0.11 mmol) in anhydrous DMF (3 mL) under argon was added benzylbromide (16 μl, 0.13 mmol) followed by sodium hydride (6.3 mg, 0.16 mmol) and the reaction stirred for 16 h. Solvent was removed in vacuo and the residue partitioned between ethyl acetate (2×20 mL) and water (20 mL). The organic fractions were washed with 1M HCl (20 mL), NaHCO3 (2×20 mL) then brine (2×20 mL), dried (MgSO4) and the solvent removed in vacuo. Crude material was purified by chromatography on silica gel with dichloromethane/methanol (9:1) as the eluent to give the title compound as an off-white powder. m/z (ES+)=535.33 [M+H]+; RT=3.44 min.

후처리

  1. customSolvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (2×20 mL) and water (20 mL)
  3. washThe organic fractions were washed with 1M HCl (20 mL), NaHCO3 (2×20 mL)
  4. dry with materialbrine (2×20 mL), dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customCrude material was purified by chromatography on silica gel with dichloromethane/methanol (9:1) as the eluent

출처 및 근거

ORD 기록
ord-31e8ca724c7f4886b84060221d44cc67
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158622B2

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