6-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine → 2-[4-[(6-Chloroimidazo[1,2-a]pyridin-2-yl)methyl]-1-piperazinyl]-4-fluorobenzonitrile

HRID 1416287

반응식

HRID 1416287 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11]Cl)[N:10]=2)[CH:7]=1.[C:13]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)#[N:14]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:25]3[CH2:24][CH2:23][N:22]([C:16]4[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]=4[C:13]#[N:14])[CH2:27][CH2:26]3)[N:10]=2)[CH:7]=1

참가 물질

4

반응물 2

HCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridineHCID 193671084-Fluoro-2-(piperazin-1-yl)benzonitrile

생성물 1

HCID 193671472-[4-[(6-Chloroimidazo[1,2-a]pyridin-2-yl)methyl]-1-piperazinyl]-4-fluorobenzonitrile수율 63.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Following the general procedure of Example 39, Step 2, and making non-critical variations, 6-chloro-2-(chloromethyl)imidazo[1,2-α]pyridine (Example 4, Step 1; 0.298 g), 1-(2-cyano-5-fluorophenyl)piperazine (0.309 g), and THF (2 mL) are converted to product, which is then chromatographed on silica gel using methanol/dichlormethane (2/98 to 4/96). Crystallization from dichloromethane/hexane, gives 0.348 g of material, which is recrystallized from ethyl acetate/dichloromethane to give 0.201 g of the title compound; mp 149-150° C.; MS m/z 369, 371; IR (mineral oil) 1625, 1260, 2221, 1514, 1332 cm-1 ; 1H NMR (CDCl3) δ2.69, 3.37, 3.76, 3.53, 6.61, 7.13, 7.39, 7.52, 7.53, 8.14.

후처리

  1. customis then chromatographed on silica gel
  2. customCrystallization from dichloromethane/hexane

출처 및 근거

ORD 기록
ord-4156ec3d39d042eeb4aebd5760cc228e
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05912246

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