Piperidine → HCID 59314293, compound

HRID 1047937Notes

Reaction equation

HRID 1047937 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][C:19]=2F)=[O:17])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].[NH:25]1[CH2:30]CC[CH2:27][CH2:26]1.O1CCOC[CH2:32]1>>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][C:19]=2[N:25]([CH:26]([CH3:32])[CH3:27])[CH3:30])=[O:17])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 8082PiperidineHCID 312751,4-DioxaneHCID 59314249HCID 59314249, compound

Product 1

HCID 59314293HCID 59314293, compound

Procedure

A 10 mL microwave reaction vessel is charged with 2-[(3-fluoro-pyridine-4-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (354, 500 mg, 1.52 mmol), 1,4-dioxane (2 mL) and piperidine 2 mL, 29.5 mmol). A stirring bar is added. The reaction vial is crimped sealed. The reaction vial is placed in a Smith Microwave reaction apparatus. The temperature is set for 150° C. with a fixed hold time of 10 min. Pre-stir time is set for 20 sec. After this sequence is completed, the reaction vial is removed from the apparatus. The stirring bar is extracted. The contents of the flask are transferred to a round bottom flask and the solvent removed under reduced pressure. Pumping to a constant weight gives 0.71 g of brown syrup. This is dissolved in DCM (10 mL) and applied to an ISCO Companion that is fitted with a 40 g column (silica). The column is eluted with EtOAc/heptanes (5%) for 4 column volumes followed by a linear gradient to 65% EtOAc/heptanes over 10 column volumes and then 90% EtOAc/heptanes for 2 column volumes. 14 mL fractions of UV active eluent are collected. Fractions 5-11 are combined and evaporated by pumping to constant weight to give 0.29 g of an amorphous white solid (0.29 g, 51%).

Workup

  1. additionA stirring bar is added
  2. customThe reaction vial is crimped sealed
  3. customThe reaction
  4. customvial is placed in a Smith Microwave reaction apparatus
  5. customis set for 150° C. with a fixed hold time of 10 min
  6. customthe reaction
  7. customvial is removed from the apparatus
  8. extractionThe stirring bar is extracted
  9. customThe contents of the flask are transferred to a round bottom flask
  10. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-94c67ef6c8db4c61bf08ba8d04dcee18
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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