Dimethylformamide → HCID 178438012, compound

HRID 2240166Notes

Reaction equation

HRID 2240166 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=O)=[CH:9][CH:10]=2)[NH:5][N:4]=1)[CH3:2].Cl.CN(C)CCCN=C=NCC.Cl.[CH3:28][NH:29][O:30][CH3:31].CN(C)C=O>CN(C)C1C=CN=CC=1.C(Cl)Cl.O>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([N:29]([O:30][CH3:31])[CH3:28])=[O:14])=[CH:9][CH:10]=2)[NH:5][N:4]=1)[CH3:2]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178438013HCID 178438013, compound

Product 1

HCID 178438012HCID 178438012, compoundYield 34.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-ethyl-1H-indazole-6-carboxylic acid (3.9 g, 0.020 mol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (4.3 g, 0.022 mol) and 4-dimethylaminopyridine (3.11 g, 0.0254 mol), N,O-dimethylhydroxylamin hydrochloride (2.8 g, 0.028 mol) were dissolved in methylene chloride (200 mL) and N,N-dimethylformamide (20 mid) and the solution stirred at room temperature for one hour. The resulting mixture was poured in iced water. The aqueous layer was removed, and extracted with ethyl acetate (2×50 mL). The combined organics were washed with 1 N HCl, 2N NaOH, water, and brine, then dried. The solvent was removed in vacuo, and the residue was purified by column chromatography on silica gel eluting with a gradient of 50% ethyl acetate in hexanes to 100% ethyl acetate over 30 minutes to give 1.6 g (33%) of 3-ethyl-N-methoxy-N-methyl-1H-indazole-6-carboxamide.

Workup

  1. customThe aqueous layer was removed
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washThe combined organics were washed with 1 N HCl, 2N NaOH, water, and brine
  4. customdried
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by column chromatography on silica gel eluting with a gradient of 50% ethyl acetate in hexanes to 100% ethyl acetate over 30 minutes

Sources & evidence

ORD record
ord-38a447b76611448b971fb37fad6a0c03
Source dataset
uspto-grants-2010_05
Patent number
US07723348B2

Reaction notes

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