Ethylmorpholine → HCID 11689242, compound

HRID 733660Notes

Reaction equation

HRID 733660 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]3[NH:15][CH:16]=[C:17]([CH3:18])[C:13]=3[C:12]([C:19]([OH:21])=O)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.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>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:10]=[CH:11][C:12]([C:19]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:21])=[C:13]3[C:17]([CH3:18])=[CH:16][NH:15][C:14]=23)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57840790HCID 57840790, compound

Product 1

HCID 11689242HCID 11689242, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(3-chloro-phenylamino)-3-methyl-1H-pyrrolo[2,3-c]pyridine-4-carboxylic acid (34 mg) in dimethylformamide (2 ml) was added 4-ethylmorpholine (57 μl), morpholine (19 μl), 1-hydroxybenzotriazole hydrate (24 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (26 mg) and the solution stirred at room temperature overnight. The dimethylformamide was evaporated and the residue triturated with 5% sodium bicarbonate to give an off white solid. The solid was filtered, washed thoroughly with water, and dried over sodium hydroxide at 50° C. to afford 1-[7-(3-chloro-phenylamino)-3-methyl-1H-pyrrolo[2,3-c]pyridin-4-yl]-1-morpholin-4-yl-methanone (22 mg).

Workup

  1. customThe dimethylformamide was evaporated
  2. customthe residue triturated with 5% sodium bicarbonate
  3. customto give an off white solid
  4. filtrationThe solid was filtered
  5. washwashed thoroughly with water
  6. dry with materialdried over sodium hydroxide at 50° C.

Sources & evidence

ORD record
ord-361a71986b6e4898b5b8e242a0983952
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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