6-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine → HCID 19367095, compound

HRID 1416261Notes

Reaction equation

HRID 1416261 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.[N:13]1([C:19]2[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=2[C:21]([NH2:23])=[O:22])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:16]3[CH2:15][CH2:14][N:13]([C:19]4[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=4[C:21]([NH2:23])=[O:22])[CH2:18][CH2:17]3)[N:10]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 48683896-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridineHCID 106558542-Piperazin-1-yl-benzamide

Product 1

HCID 19367095HCID 19367095, compoundYield 41.9%

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; 0.306 g) and 2-(piperazin-1-yl)benzamide (0.336 g) are converted to 0.236 g of the title compound after chromatography on silica gel using methanol/dichloromethane (8/92) and crystallization from ethyl acetate/dichloromethane. A portion of this material was recrystallized from ethyl acetate/methanol/hexane; mp 178-179° C.; ms m/z 369; IR (mineral oil) 1663, 3289, 1325, 1448, 796 cm-1 ; 1H NMR (CDCl3) δ2.75, 3.08, 3.78, 5.76, 7.13, 7.23, 7.46, 7.52, 7.53, 8.14, 8.17, 9.57.

Sources & evidence

ORD record
ord-a78fff8a642f47be89b1f091f624d934
Source dataset
uspto-grants-1999_06
Patent number
US05912246

Reaction notes

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