Ethylmorpholine → HCID 57840771, compound

HRID 733668Notes

Reaction equation

HRID 733668 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[C:13]([Cl:20])=[N:14][CH:15]=[C:16]([C:17]([OH:19])=O)[C:11]=2[C:10]([CH3:21])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)C.N1CCOCC1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:12]2=[C:13]([Cl:20])[N:14]=[CH:15][C:16]([C:17]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:19])=[C:11]2[C:10]([CH3:21])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 7525EthylmorpholineHCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 44475513HCID 44475513, compound

Product 1

HCID 57840771HCID 57840771, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-chloro-3-methyl-pyrrolo[2,3-c]pyridine-1,4-dicarboxylic acid 1-tert-butyl ester (300 mg) in dimethylformamide (4 ml) was added 4-ethylmorpholine (492 ul), morpholine (172 ul), 1-hydroxybenzotriazole hydrate (204 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (223 mg) and the solution stirred at room temperature overnight. The solution was diluted with ethyl acetate (50 ml). The organic layer was then washed with 5% sodium hydrogen carbonate solution (2×10 ml) and water (2×20 ml). The organic layer was dried (MgSO4) and evaporated to give an off-white foam (107 mg) which was used without further purification.

Workup

  1. washThe organic layer was then washed with 5% sodium hydrogen carbonate solution (2×10 ml) and water (2×20 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-2cee91cb58044bcb95b123b84c9b16d3
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

Loading…