Triethylamine → N2-(2-aminophenyl)-N6-pyridin-3-yl-4,7-dihydrothieno[2,3-c]pyridine-2,6(5H)-dicarboxamide

HRID 2093102Notes

Reaction equation

HRID 2093102 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[S:19][C:14]2[CH2:15][NH:16][CH2:17][CH2:18][C:13]=2[CH:12]=1)=[O:10].CCN(CC)CC.[N+](C1C=CC([O:36][C:37](=O)[NH:38][C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)=CC=1)([O-])=O>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[S:19][C:14]2[CH2:15][N:16]([C:37]([NH:38][C:39]3[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=3)=[O:36])[CH2:17][CH2:18][C:13]=2[CH:12]=1)=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 100611013-PYRIDINYLCARBAMIC ACID 4-NITROPHENYL ESTERHCID 58117017N-(2-aminophenyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-2-carboxamide

Product 1

HCID 25230191N2-(2-aminophenyl)-N6-pyridin-3-yl-4,7-dihydrothieno[2,3-c]pyridine-2,6(5H)-dicarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(2-aminophenyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-2-carboxamide (1.0 eq) in DMF was added Et3N (3.0 eq.) followed by pyridin-3-yl-carbamic acid 4-nitro-phenyl ester (1.0 eq) and reaction was stirred at room temperature overnight. Reaction mixture was then quenched with water and extracted with dichloromethane. The organic layer was separated, dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the title compound.

Workup

  1. customReaction mixture
  2. customwas then quenched with water
  3. extractionextracted with dichloromethane
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto afford crude product, which
  8. customon purification by column chromatography

Sources & evidence

ORD record
ord-36e6111cb15f49a3aad7400d85171917
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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