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Furfurylamine → HCID 178523028, compound

HRID 34027
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Reaction equation

HRID 34027 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:19]([OH:21])=O)[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[C:7]2/[CH:11]=[CH:12]/[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.C(N(CC)C(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1.[CH2:42]([NH2:48])[C:43]1[O:47][CH:46]=[CH:45][CH:44]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O.C(OCC)(=O)C>[O:47]1[CH:46]=[CH:45][CH:44]=[C:43]1[CH2:42][NH:48][C:19]([C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([F:1])[CH:3]=1)[NH:9][N:8]=[C:7]2/[CH:11]=[CH:12]/[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 3438FurfurylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178524526HCID 178524526, compound

Product 1

HCID 178523028
HCID 178523028, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

376 mg of 7-fluoro-3-[(E)-2-(pyridin-3-yl)-vinyl]-1H-indazole-5-carboxylic acid was dissolved in 10 mL of N,N-dimethylformamide, and added with 903 μl of N,N-diisopropylethylamine, 244 mg of 1-hydroxybenzotriazole monohydrate and 147 μl of furfurylamine, and stirred at room temperature for 10 minutes. The solution was cooled to 0° C., added with 509 mg of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride, and stirred at room temperature overnight. After diluting with water and ethyl acetate, the organic phase was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was evaporated, and the resultant crude product was purified by silica gel column chromatography, to afford 159 mg of the title compound as yellow crystals.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. stirringstirred at room temperature overnight
  3. washthe organic phase was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe resultant crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-269af998a4324c23b25959beee1b4acf
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07429609B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes