Hydrochloric Acid → 1-(3-Phenyl-2-chloropyrid-6-ylmethyl)-5-(4-cyanobenzyl)imidazole hydrochloride salt

HRID 363198노트

반응식

HRID 363198 반응식
C([N:20]1[CH:24]=[C:23]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=2)[N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:34]1([C:40]2[C:41]([Cl:48])=[N:42][C:43]([CH2:46]Br)=[CH:44][CH:45]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.Cl>C(#N)C.CO>[ClH:48].[C:34]1([C:40]2[C:41]([Cl:48])=[N:42][C:43]([CH2:46][N:22]3[C:23]([CH2:25][C:26]4[CH:27]=[CH:28][C:29]([C:32]#[N:33])=[CH:30][CH:31]=4)=[CH:24][N:20]=[CH:21]3)=[CH:44][CH:45]=2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric Acid2회HCID 158375331-Trityl-4-(4-cyanobenzyl)imidazoleHCID 543404513-Phenyl-2-chloro-6-bromomethylpyridine

생성물 1

HCID 867537371-(3-Phenyl-2-chloropyrid-6-ylmethyl)-5-(4-cyanobenzyl)imidazole hydrochloride salt

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매2회

반응 조건

온도
65 °C

실험 절차

To 1-trityl-4-(4-Cyanobenzyl)-imidazole (88.4 mg, 0.208 mmol) in acetonitrile (1 mL) was added 3-phenyl-2-chloro-6-bromomethylpyridine (53.5 mg, 0.189 mmol) and the mixture heated at 65° C. for 16 hours. The residue was dissolved in methanol (3 ml) and heated at reflux for 2 hours, cooled and evaporated to dryness. The residue was partitioned between sat. aq. Na2CO3 solution and CH2Cl2. The organic layer was dried, (MgSO4) and the solvent evaporated in vacuo. The residue was chromatographed (Silica gel, 2.5-3% MeOH in CH2Cl2) to afford the free base which was converted to the HCl salt by treatment with one equivalent of HCl in aqueous acetonitrile. Evaporation of solvent in vacuo afforded the title compound as a white powder.

후처리

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperaturecooled
  4. customevaporated to dryness
  5. customThe residue was partitioned between sat. aq. Na2CO3 solution and CH2Cl2
  6. customThe organic layer was dried
  7. custom(MgSO4) and the solvent evaporated in vacuo
  8. customThe residue was chromatographed (Silica gel, 2.5-3% MeOH in CH2Cl2)
  9. customto afford the free base which
  10. customEvaporation of solvent in vacuo

출처 및 근거

ORD 기록
ord-fac46232c01e4bd9a1edbc7d191fcc30
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05872136

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