Chloromethyl Methyl Ether → HCID 11305377, compound

HRID 1244321Notes

Reaction equation

HRID 1244321 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, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

0.3 g 5-Chloro-2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3H-imidazo[4,5-b]pyridine (0.74 mmol) was dissolved in dry DMF (10.0 ml) and treated with 0.033 g NaH (65% in oil, 0.9 mmol) at 0° C. After stirring at ambient temperature for 1 h, 68 μl MOMCl (0.9 mmol) and 0.011 g tetrabutyl ammonium iodide (0.03 mmol) were added and the reaction mixture was stirred for 16 h. The suspension was filtered and the residue triturated in ether. Upon drying in vacuo, one obtained 0.29 g of 5-chloro-3-methoxymethyl-2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3H-imidazo[4,5-b]pyridine (87%) as a yellow solid; M.p.: 167–170° C.

Workup

  1. stirringthe reaction mixture was stirred for 16 h
  2. filtrationThe suspension was filtered
  3. customthe residue triturated in ether
  4. customUpon drying in vacuo, one

Sources & evidence

ORD record
ord-b7f3b99b869548338d11160e0f640ab4
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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