Triethylamine → N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-formylhydrazinecarbonyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79348Notes

Reaction equation

HRID 79348 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([C:24]([OH:26])=O)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[N:29]=2)[N:4]=1)[CH3:2].[CH:35]([NH:37][NH2:38])=[O:36].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([C:24]([NH:38][NH:37][CH:35]=[O:36])=[O:26])=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH3:34])[N:29]=2)[N:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12229HydrazinecarboxaldehydeHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 672601493-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridine-7-carboxylic acid

Product 1

HCID 67260976N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(2-formylhydrazinecarbonyl)imidazo[1,2-a]pyridine-3-carboxamideYield 70.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To 3-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-ylcarbamoyl)imidazo[1,2-a]pyridine-7-carboxylic acid (26 mg, 0.057 mmol; prepared as in Example 28, Step A) in DMF was added formohydrazide (6.9 mg, 0.11 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (22 mg, 0.11 mmol), 1H-benzo[c/][1,2,3]triazol-1-ol hydrate (15 mg, 0.11 mmol) and triethylamine (17 mg, 0.17 mmol). The reaction mixture was stirred for 16 hours at ambient temperature, diluted with DCM (30 mL), washed with H2O, dried (Na2SO4) and concentrated under reduced pressure. The residue was triturated with Et2O (30 mL) to give the product (20 mg).

Workup

  1. washwashed with H2O
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with Et2O (30 mL)

Sources & evidence

ORD record
ord-009cc147dfad468582c986530bee1761
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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