Ethylmorpholine → 4-Chloro-1-methyl-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridine

HRID 733724Notes

Reaction equation

HRID 733724 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10]([CH3:11])[C:6]=2[C:5]([C:12]([OH:14])=O)=[CH:4][N:3]=1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C([N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1)C.N1CCOCC1>CN(C)C=O.O>[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10]([CH3:11])[C:6]=2[C:5]([C:12]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)=[O:14])=[CH:4][N:3]=1

Participants

8

Reactant 5

HCID 7525EthylmorpholineHCID 8083MorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 578409034-Chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid

Product 1

HCID 578410404-Chloro-1-methyl-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid (660 mg) in dimethylformamide (10 ml) was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (1.21 g), 1-hydroxybenzotriazole (0.86 g), N-ethylmorpholine (0.8 ml) and morpholine (0.55 ml). The solution was stirred at room temperature overnight. The reaction was diluted with water and extracted three times with ethyl acetate. The ethyl acetate layers were combined, washed with saturated sodium chloride solution and dried (MgSO4) then evaporated to afford the title compound as an off-white solid (783 mg). This was carried through without further purification.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. customthen evaporated

Sources & evidence

ORD record
ord-c034bcd4aaaf4fe4934334a5284cd160
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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