Ethylmorpholine → HCID 57840793, compound

HRID 733679Notes

Reaction equation

HRID 733679 reaction equation
[Cl:1][C:2]1[C:7]2[NH:8][CH:9]=[CH:10][C:6]=2[C:5]([C:11]([OH:13])=O)=[CH:4][N:3]=1.C(N1CCOCC1)C.[O:22]1[CH2:27][CH2:26][CH:25]([CH2:28][NH2:29])[CH2:24][CH2:23]1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[O:22]1[CH2:27][CH2:26][CH:25]([CH2:28][NH:29][C:11]([C:5]2[C:6]3[CH:10]=[CH:9][NH:8][C:7]=3[C:2]([Cl:1])=[N:3][CH:4]=2)=[O:13])[CH2:24][CH2:23]1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27732104-AminomethyltetrahydropyranHCID 27960291-Hydroxybenzotriazole hydrateHCID 578408437-chloro-1H-pyrrolo[2,3-c]pyridine-4-carboxylic acid

Product 1

HCID 57840793HCID 57840793, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-chloro-1H-pyrrolo[2,3-c]pyridine-4-carboxylic acid (110 mg) in dimethylformamide (4 ml) was added 4-ethylmorpholine (187 μl), tetrahydro-pyran-4-ylmethylamine (97 mg), 1-hydroxybenzotriazole hydrate (118 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (129 mg) and the solution stirred at room temperature overnight. The dimethylformamide was evaporated and the residue dissolved in ethyl acetate (10 ml). The organic layer was then washed with 5% sodium hydrogen carbonate solution (4 ml) and brine (4 ml). The organic layer was dried (MgSO4) and evaporated to give a pale orange solid. The solid was triturated with diethyl ether and then filtered off, sucked dry then dried at 40° C. under vacuum to afford the title compound (93 mg).

Workup

  1. customThe dimethylformamide was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate (10 ml)
  3. washThe organic layer was then washed with 5% sodium hydrogen carbonate solution (4 ml) and brine (4 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated
  6. customto give a pale orange solid
  7. customThe solid was triturated with diethyl ether
  8. filtrationfiltered off
  9. customsucked dry
  10. customthen dried at 40° C. under vacuum

Sources & evidence

ORD record
ord-3edbe2e917894c798517cf8153eeef79
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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