Triethylamine → Pyridine-3-carboxylic acid N'-(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)hydrazide

HRID 1362933

Reaction equation

HRID 1362933 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C(N(CC)CC)C.[Cl:18][C:19]1[CH:20]=[C:21]2[CH:27]=[C:26]([C:28](O)=[O:29])[NH:25][C:22]2=[CH:23][N:24]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[Cl:18][C:19]1[CH:20]=[C:21]2[CH:27]=[C:26]([C:28]([NH:10][NH:9][C:1]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=3)=[O:8])=[O:29])[NH:25][C:22]2=[CH:23][N:24]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 11112Nicotinic acid, hydrazideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 446307045-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

Product 1

HCID 59830438Pyridine-3-carboxylic acid N'-(5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carbonyl)hydrazide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of nicotinic acid hydrazide (35 mg, 0.25 mmol) in DMF (5 mL) was added triethylamine (88 μL, 0.64 mmol), 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (Preparation 8, 50 mg, 0.25 mmol), HOBt (34 mg, 0.25 mmol) and EDCI (50 mg, 0.28 mmol). The mixture was allowed to stir at rt for 16 h. The solvent was removed in vacuo and the residue was partitioned between water (100 mL) and ethyl acetate (100 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to give an oil, which was purified by flash chromatography on silica gel (dichloromethane/methanol, 9/1) to give the title compound. m/z (ES+)=316 [M+H]+; RT=2.62 min.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between water (100 mL) and ethyl acetate (100 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give an oil, which
  6. customwas purified by flash chromatography on silica gel (dichloromethane/methanol, 9/1)

Sources & evidence

ORD record
ord-289e93d2f1644254a1d4659a32b7a4aa
Source dataset
uspto-grants-2011_02
Patent number
US07884112B2

Linked notes

Loading…