Ethylmorpholine → N-(3-Chlorophenyl)-1-methyl-7-(4-thiomorpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-4-amine

HRID 733727Notes

Reaction equation

HRID 733727 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]3[CH:15]=[CH:16][N: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.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N1CCOCC1)C.[NH:51]1[CH2:56][CH2:55][S:54][CH2:53][CH2:52]1>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:14]3[CH:15]=[CH:16][N:17]([CH3:18])[C:13]=3[C:12]([C:19]([N:51]3[CH2:56][CH2:55][S:54][CH2:53][CH2:52]3)=[O:21])=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 7525EthylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 67164ThiomorpholineHCID 757711-HydroxybenzotriazoleHCID 44475510HCID 44475510, compound

Product 1

HCID 57841005N-(3-Chlorophenyl)-1-methyl-7-(4-thiomorpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-4-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[(3-chlorophenyl)amino]-1-methyl-1H-pyrrolo[3,2-c]pyridine-7-carboxylic acid (0.2 g) in dimethylformamide (5 ml) was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (0.15 g), 1-hydroxybenzotriazole (0.14 g), N-ethylmorpholine (0.34 ml) and thiomorpholine (0.13 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 bicarbonate solution followed by saturated sodium chloride solution then dried (MgSO4) and evaporated. The residue was purified by MDAP to afford the title compound as a white solid (236 mg).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialthen dried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by MDAP

Sources & evidence

ORD record
ord-55c07c44c61142fb8a69a5602be195fe
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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