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Ethyl Acetate → 4-[1-(4-Cyano-3-fluorobenzyl)-5-imidazolylmethyl]-1-[3-hydroxybenzyl]-2-piperazinone

HRID 412124
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인쇄 미리보기

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HRID 412124 반응식
Cl.[OH:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[CH2:6][N:7]1[CH2:12][CH2:11][NH:10][CH2:9][C:8]1=[O:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:31]([C:33]1[CH:46]=[CH:45][C:36]([CH2:37][N:38]2[C:42]([CH:43]=O)=[CH:41][N:40]=[CH:39]2)=[CH:35][C:34]=1[F:47])#[N:32].CCOC(C)=O>ClCCCl>[C:31]([C:33]1[CH:46]=[CH:45][C:36]([CH2:37][N:38]2[C:42]([CH2:43][N:10]3[CH2:11][CH2:12][N:7]([CH2:6][C:5]4[CH:14]=[CH:15][CH:16]=[C:3]([OH:2])[CH:4]=4)[C:8](=[O:13])[CH2:9]3)=[CH:41][N:40]=[CH:39]2)=[CH:35][C:34]=1[F:47])#[N:32]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 114247081-(4-Cyano-3-fluorobenzyl)-5-imidazolecarboxaldehydeHCID 185360721-[3-(Hydroxy)benzyl]-2-piperazinone hydrochloride

생성물 1

HCID 185360964-[1-(4-Cyano-3-fluorobenzyl)-5-imidazolylmethyl]-1-[3-hydroxybenzyl]-2-piperazinone

시약·촉매·용매 1

HCID 11
1,2-Dichloroethane
용매

실험 절차

To a solution of the amine hydrochloride from Step K (theoretically 0.22 mmol) in 2 mL of 1,2-dichloroethane was added 4 Å powdered molecular sieves (100 mg), followed by sodium triacetoxyborohydride (70 mg, 0.33 mmol). The aldehyde from Step G (51 mg, 0.22 mmol) was added, and the reaction was stirred for 16 hours. The reaction was poured into EtOAc, washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The titled product was obtained as a pale yellow foam.

후처리

  1. washwashed with sat. aq. NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-404df1de74b948a895ff4ee99db0dcec
출처 데이터셋
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06562823B1

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