Chloromethyl Methyl Ether → HCID 11305377, compound

HRID 1244300Notes

Reaction equation

HRID 1244300 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][C:9]([C:11]3[S:12][C:13]4[C:19]([N:20]5[CH2:25][CH2:24][O:23][CH2:22][CH2:21]5)=[CH:18][CH:17]=[C:16]([O:26][CH3:27])[C:14]=4[N:15]=3)=[N:10][C:5]2=[CH:4][CH:3]=1.[H-].[Na+].[CH2:30](Cl)[O:31][CH3:32]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:30][O:31][CH3:32])[C:9]([C:11]3[S:12][C:13]4[C:19]([N:20]5[CH2:25][CH2:24][O:23][CH2:22][CH2:21]5)=[CH:18][CH:17]=[C:16]([O:26][CH3:27])[C:14]=4[N:15]=3)=[N:10][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 178491999HCID 178491999, compound

Product 1

HCID 11305377HCID 11305377, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Furthermore, 5-chloro-2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3H-imidazo[4,5-b]pyridine (for R1=morpholinyl, Ic2) was dissolved in dry DMF and treated with NaH at 0° C. After stirring at ambient temperature for 1 h MOMCl and tetrabutyl ammonium iodide were added and the reaction mixture was stirred for about 16 h. The suspension was worked up to obtain the corresponding 5-chloro-3-methoxymethyl-2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3H-imidazo[4,5-b]pyridine (Ic4), which was dissolved in morpholine (for R5=morpholin) in an autoclave and heated to about 150° C. for 16 h. The residue was triturated in water whereupon the precipitate was worked up to obtain the corresponding 3-methoxymethyl-2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-5-morpholin-4-yl-3H-imidazo[4,5-b]pyridine (Ic5). The corresponding 2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-5-morpholin-4-yl-3H-imidazo[4,5-b]pyridine (Ic1) was obtained by treating with HCl for about 1.5 h.

Workup

  1. additionwere added

Sources & evidence

ORD record
ord-a4f5b3de36f64ad197a11dc9bae86e8e
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

Loading…