Tetrahydrofuran → HCID 22936650, compound

HRID 387825Notes

Reaction equation

HRID 387825 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[CH:7]1([NH:10][C:11]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([O:22][C:23]4[CH:28]=[CH:27][N:26]=[C:25]([NH2:29])[CH:24]=4)=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)=[O:12])[CH2:9][CH2:8]1.C(N(CC)CC)C.[O:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1>>[CH:7]1([NH:10][C:11]([N:13]2[C:21]3[C:16](=[CH:17][C:18]([O:22][C:23]4[CH:28]=[CH:27][N:26]=[C:25]([N:29]([C:41]([CH:40]5[CH2:38][CH2:39]5)=[O:37])[C:4]([CH:1]5[CH2:3][CH2:2]5)=[O:5])[CH:24]=4)=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)=[O:12])[CH2:9][CH2:8]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 21949236N1-cyclopropyl-5-((2-amino-4-pyridyl)oxy)-1H-1-indolecarboxamide

Product 1

HCID 22936650HCID 22936650, compound

Procedure

Cyclopropanecarbonyl chloride (51 mg) was added to a solution of 100 mg of N1-cyclopropyl-5-[(2-amino-4-pyridyl)oxy]-1H-1-indolecarboxamide and 49 mg of triethylamine in tetrahydrofuran at 0° C. After 20 minutes of stirring, silica gel was added to the reaction solution, the solvent was distilled off under reduced pressure, and the reaction product was adsorbed onto the silica gel. The silica gel was charged into a dry column packed with silica gel, and purification was performed by column chromatography (hexane:ethyl acetate=1:1, followed by ethyl acetate), after which water was added to the residue to obtain 19 mg of the target substance as a white solid.

Workup

  1. additionsilica gel was added to the reaction solution
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionThe silica gel was charged into a dry column
  4. custompacked with silica gel, and purification
  5. additionafter which water was added to the residue
  6. customto obtain 19 mg of the target substance as a white solid

Sources & evidence

ORD record
ord-e0f3d850738f45758d48a4fe30d357d3
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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