Piperidine → N-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-methoxyacetamide

HRID 2365060Notes

Reaction equation

HRID 2365060 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=CC3NC4CCN(CCN(CC)CC)C(=O)C=4C=3C)[C:7](=[O:11])[NH:8]2)=[CH:4][C:3]=1[F:31].N1CCCCC1.[CH3:38][O:39][CH2:40][C:41](Cl)=[O:42]>O1CCCC1>[F:31][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[NH:1][C:41](=[O:42])[CH2:40][O:39][CH3:38])[NH:8][C:7](=[O:11])[CH2:6]2

Participants

5

Reactant 3

HCID 8082PiperidineHCID 96623Methoxyacetyl chlorideHCID 666072882-(6-Amino-5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-(2-diethylamino-ethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-one

Product 1

HCID 45118148N-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-methoxyacetamideYield 69.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-50 °C

Procedure

A stirred solution of d 6-amino-5-fluoro-1,3-dihydro-indol-2-one (2.028 g, 12.2 mmol) obtained from Example 7 in 30 ml of tetrahydrofuran was added with piperidine (1.3 ml). The mixture was cooled to −50° C. in an ethanol-dry ice bath and added with methoxyacetyl chloride (1.35 g, 12.5 mmol) in 20 ml of tetrahydrofuran dropwise. Upon the completion of the addition, the resulting mixture was stirred at the room temperature overnight until the precipitate was formed. The solid was filtered, washed with water and recrystallized from methanol to give N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-methoxy-acetamide (2.0 g, 69.2%) as a white solid.

Workup

  1. additionUpon the completion of the addition
  2. customwas formed
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-220aabd5860d4a849455994923277d0c
Source dataset
uspto-grants-2014_04
Patent number
US08697692B2

Reaction notes

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