Triethylamine → N2-(2-aminophenyl)-1-methyl-N5-pyridin-3-yl-1,4,6,7-tetrahydro-5H-pyrrolo[3,2-c]pyridine-2,5-dicarboxamide

HRID 2093098Notes

Reaction equation

HRID 2093098 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[N:19]([CH3:20])[C:18]2[CH2:17][CH2:16][NH:15][CH2:14][C:13]=2[CH:12]=1)=[O:10].CCN(CC)CC.C1([O:34][C:35](=O)[NH:36][C:37]2[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=2)C=CC=CC=1>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[N:19]([CH3:20])[C:18]2[CH2:17][CH2:16][N:15]([C:35]([NH:36][C:37]3[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=3)=[O:34])[CH2:14][C:13]=2[CH:12]=1)=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 58117020HCID 58117020, compound

Product 1

HCID 25230113N2-(2-aminophenyl)-1-methyl-N5-pyridin-3-yl-1,4,6,7-tetrahydro-5H-pyrrolo[3,2-c]pyridine-2,5-dicarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound N-(2-aminophenyl)-1-methyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carboxamide (1.0 eq) in DMF was added Et3N (3.0 eq.) followed by Pyridin-3-yl-carbamic acid phenyl ester (1.0 eq). Reaction was stirred at room temperature for overnight. Reaction mixture was then quenched with water and extracted with ethyl acetate, dried over sodium sulphate and concentrated to dryness. Crude mass was then purified by silica gel column chromatography to afford N2-(2-aminophenyl)-1-methyl-N5-pyridin-3-yl-1,4,6,7-tetrahydro-5H-pyrrolo[3,2-c]pyridine-2,5-dicarboxamide.

Workup

  1. customReaction
  2. customReaction mixture
  3. customwas then quenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated to dryness
  7. customCrude mass was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a216e84ae98c458d84c2ead19d1b2226
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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