Diisopropyl Ether → HCID 131734743, compound

HRID 2207749Notes

Reaction equation

HRID 2207749 reaction equation
C(NCC[C:7]1[C:15]2[C:10](=[CH:11][C:12]([F:18])=[C:13]([O:16][CH3:17])[CH:14]=2)[NH:9][C:8]=1[C:19]([OH:21])=O)(=O)C.[Cl-].[NH4+].O[N:25]1[C:29]2[CH:30]=CC=CC=2N=N1.Cl.C([N:37]=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+].[CH:51]([O:54]C(C)C)(C)[CH3:52]>C(OCC)(=O)C.C(N(CC)CC)C.C(#N)C>[C:51]([NH:25][CH2:29][CH2:30][N:9]1[C:10]2[C:15](=[CH:14][C:13]([O:16][CH3:17])=[C:12]([F:18])[CH:11]=2)[CH:7]=[C:8]1[C:19]([NH2:37])=[O:21])(=[O:54])[CH3:52]

Participants

10

Reactant 6

HCID 7914Diisopropyl EtherHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89933016HCID 89933016, compound

Product 1

HCID 131734743HCID 131734743, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 3-(2-acetamidoethyl)-6-fluoro-5-methoxy-1H-indole-2-carboxylic acid (200 mg), ammonium chloride (110 mg), 1-hydroxybenzotriazole (140 mg), and acetonitrile (4.00 mL) were added triethylamine (0.300 mL) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (200 mg), followed by stirring at room temperature overnight. To the mixture was added an aqueous sodium hydrogen carbonate solution, followed by extraction with chloroform, and the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=96:4 to 9:1). To the obtained crude product was added ethyl acetate, followed by heating. Then, diisopropylether was added thereto, followed by stirring at room temperature. The resulting solid was collected by filtration and dried under reduced pressure to obtain 3-(2-acetamidoethyl-6-fluoro-5-methoxy-1H-indole-2-carboxamide (153 mg) as a white solid.

Workup

  1. extractionfollowed by extraction with chloroform
  2. concentrationthe organic layer was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=96:4 to 9:1)
  4. customTo the obtained crude product
  5. temperatureby heating
  6. stirringby stirring at room temperature
  7. filtrationThe resulting solid was collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-3bc25374b2a24e269f6c39e26b7b8fee
Source dataset
uspto-grants-2016_06
Patent number
US09376449B2

Reaction notes

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