6-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine → HCID 19367132, compound

HRID 1416274Notes

Reaction equation

HRID 1416274 reaction equation
[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.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[C:18]([CH:21]=1)[C:19]#[N:20]>>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([N:22]2[CH2:23][CH2:24][N:25]([CH2:11][C:9]3[N:10]=[C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]4[CH:8]=3)[CH2:26][CH2:27]2)=[C:18]([CH:21]=1)[C:19]#[N:20]

Participants

3

Reactant 2

HCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridineHCID 193671275-Chloro-2-(piperazin-1-yl)benzonitrile

Product 1

HCID 19367132HCID 19367132, compoundYield 62.2%

Procedure

Following the general procedure of Example 11 and making non-critical variations, 6-chloro-2-(chloromethyl)imidazo[1,2-α]pyridine (Example 4, Step 1; 0.292 g) and 5-chloro-2-(piperazin-1-yl)benzonitrile (0.385 g) are converted to 0.349 g of the title compound after chromatography on silica gel and crystallization from ethyl ether/dichloromethane/hexane. mp 191-191.5° C.; MS m/z 385, 387; IR (mineral oil) 1486, 1330, 806, 1495, 826 cm-1 ; 1H NMR (CDCl3) δ2.77, 3.24, 3.78, 6.93, 7.12, 7.42, 7.51, 8.14.

Sources & evidence

ORD record
ord-d70de81943fd48bd835440eddc924575
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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