Ethylmorpholine → HCID 57840771, compound

HRID 733664Notes

Reaction equation

HRID 733664 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: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

7

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 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-chloro-3-methyl-pyrrolo[2,3-c]pyridine-1,4-dicarboxylic acid 1-tert-butyl ester (80 mg) in dimethylformamide (2 ml) was added 4-ethylmorpholine (131 μl), morpholine (46 μl), 1-hydroxybenzotriazole hydrate (54 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (60 mg) and the solution stirred at room temperature overnight. The dimethylformamide was evaporated and the residue dissolved in ethyl acetate (20 ml). The organic layer was then washed with 5% sodium hydrogen carbonate solution (2×4 ml) and water (2×10 ml). The organic layer was dried (MgSO4) and evaporated to give a yellow oil (107 mg) which was used without further purification.

Workup

  1. customThe dimethylformamide was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate (20 ml)
  3. washThe organic layer was then washed with 5% sodium hydrogen carbonate solution (2×4 ml) and water (2×10 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-66e7309a69ea447abab75df5856eb17c
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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