Diethylene Glycol Monomethyl Ether → HCID 9983151, compound

HRID 900260Notes

Reaction equation

HRID 900260 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]([C:13]2[NH:14][C:15]([CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])=[N:16][CH:17]=2)=[O:12])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].COCCOCCO.[H-].[Na+].Br[CH2:35][C:36]([NH:38][C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][N:40]=1)=[O:37]>CN(C=O)C.COCCO>[CH:1]([N:4]1[CH2:5][CH2:6][CH:7]([NH:10][C:11]([C:13]2[N:14]([CH2:35][C:36](=[O:37])[NH:38][C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][N:40]=3)[C:15]([CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])=[N:16][CH:17]=2)=[O:12])[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8134Diethylene Glycol Monomethyl EtherHCID 24758Sodium hydrideHCID 34211102-Bromo-N-(5-chloro-2-pyridinyl)acetamide2×HCID 86594167HCID 86594167, compound

Product 1

HCID 9983151HCID 9983151, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 49 mg of 2-(2-Methoxy-ethoxymethyl)-3H-imidazole-4-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide [prepared by following the procedure from example 66 replacing 2-(2-methoxy-ethoxy)-ethanol by 2-methoxy-ethanol in step (i)] in DMF (3 mL) was added 17 mg of sodium hydride (60% in mineral oil). The mixture was stirred at 50° C. for 1 h and cooled to 30° C. 2-Bromo-N-(5-chloro-pyridin-2-yl)-acetamide (41 mg) was added and stirring was continued for 1.5 h. Another portion of 2-bromo-N-(5-chloro-pyridin-2-yl)-acetamide (10 mg) was added. The mixture was stirred for 30 min at 30° C., carefully quenched by dropwise addition of water and extracted with ethyl acetate. The combined organic phases were washed with water and brine, dried over anhydrous

Workup

  1. temperaturecooled to 30° C
  2. stirringstirring
  3. waitwas continued for 1.5 h
  4. stirringThe mixture was stirred for 30 min at 30° C.
  5. customcarefully quenched by dropwise addition of water
  6. extractionextracted with ethyl acetate
  7. washThe combined organic phases were washed with water and brine
  8. customdried over anhydrous

Sources & evidence

ORD record
ord-bf72c44974c845b985a7e30497b07bd3
Source dataset
uspto-grants-2008_04
Patent number
US07358268B2

Reaction notes

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