Triethylamine → HCID 67314690, compound

HRID 1011361Notes

Reaction equation

HRID 1011361 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:12]1[C:20]2[C:15](=[N:16][C:17]([CH:21]=[CH2:22])=[CH:18][CH:19]=2)[CH2:14][O:13]1.[OH:23][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(N(CC)CC)C>O1CCOCC1.CC(O)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:12]1[C:20]2[C:15](=[N:16][C:17]([CH2:21][CH2:22][N:27]3[CH2:28][CH2:29][CH:24]([OH:23])[CH2:25][CH2:26]3)=[CH:18][CH:19]=2)[CH2:14][O:13]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 67314553HCID 67314553, compound

Product 1

HCID 67314690HCID 67314690, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 5-fluoro-3-(2-vinyl-7H-furo[3,4-b]pyridin-5-ylidene)-1,3-dihydro-indol-2-one (50 mg, 0.17 mmol) in dioxane (10 mL) is treated with 4-hydroxypiperidine (260 mg, 2.57 mmol) and 10 drops of glacial AcOH. The reaction is stirred at 100° C. for 1 h and then cooled to room temperature. The reaction mixture is treated with triethylamine (2 mL) and is loaded onto silica gel. Purification by chromatography (silica gel) gave the title compound (57 mg, 85%).

Workup

  1. temperaturecooled to room temperature
  2. customPurification by chromatography (silica gel)

Sources & evidence

ORD record
ord-d3eea84efedb45c8835f5dd8521692e4
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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