Triethylamine → 6-methyl-N-tetrahydro-2H-pyran-4-yl-1H-indazole-5-carboxamide

HRID 1269871Notes

Reaction equation

HRID 1269871 reaction equation
Cl.[O:2]1[CH2:7][CH2:6][CH:5]([NH2:8])[CH2:4][CH2:3]1.C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH3:38][C:39]1[CH:47]=[C:46]2[C:42]([CH:43]=[N:44][NH:45]2)=[CH:41][C:40]=1[C:48](O)=[O:49].C(=O)([O-])O.[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:38][C:39]1[CH:47]=[C:46]2[C:42]([CH:43]=[N:44][NH:45]2)=[CH:41][C:40]=1[C:48]([NH:8][CH:5]1[CH2:6][CH2:7][O:2][CH2:3][CH2:4]1)=[O:49]

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 229340406-methyl-1H-indazole-5-carboxylic acidHCID 441186934-Aminotetrahydropyran hydrochloride

Product 1

HCID 694301826-methyl-N-tetrahydro-2H-pyran-4-yl-1H-indazole-5-carboxamideYield 91.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrahydro-2H-pyran-4-ylamine monohydrochloride (0.0402 g, 0.292 mmol), triethylamine (0.07 ml, 0.5 mmol), 1-hydroxybenztriazole (0.0460 g, 0.340 mmol) and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide monohydrochloride (0.0606 g, 0.316 mmol) were added to a solution of 6-methyl-1H-indazole-5-carboxylic acid (0.0437 g, 0.248 mmol) in N,N-dimethylformamide (2 ml) and stirred overnight. A saturated aqueous sodium hydrogencarbonate solution was added thereto, followed by extraction with chloroform (×3), and the extract solution was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, followed by replacement with toluene (three times), whereby a solid was precipitated. The solid obtained was suspended in ethyl acetate and stirred to be washed, and then it was collected by filtration and dried under reduced pressure to obtain 6-methyl-N-tetrahydro-2H-pyran-4-yl-1H-indazole-5-carboxamide (0.0587 g, 91%).

Workup

  1. extractionfollowed by extraction with chloroform (×3)
  2. dry with materialthe extract solution was dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customwas precipitated
  5. customThe solid obtained
  6. stirringstirred
  7. washto be washed
  8. filtrationit was collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-0474f5a605cd4320b64217c21d4b0fd8
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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