Potassium Carbonate → HCID 67517677, compound

HRID 919622Notes

Reaction equation

HRID 919622 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:22][CH:21]([NH:23]C(=O)C(F)(F)F)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CO>[Cl:8][C:6]1[CH:5]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:22][CH:21]([NH2:23])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)=[O:12])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86706479HCID 86706479, compound

Product 1

HCID 67517677HCID 67517677, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of N-(2-(2-(3,5-dichlorophenylamino)acetyl)-1,2,3,4-tetrahydroisoquinolin-4-yl)-2,2,2-trifluoroacetamide (0.45 g, 1.0 mmol), in aq. MeOH (15 mL) was added K2CO3 (1.0 g, 6.0 mmol) and the reaction mixture was heated to reflux for 2.5 h. The reaction mixture was concentrated in vacuo to give a residue which was purified by column chromatography (silica gel, gradient MeOH in DCM) to give (0.120 g, 35%) of the titled intermediate. 1H NMR (DMSO-d6, 400 MHz): δ 7.30-7.19 (m, 3H), 7.05-6.95 (m, 1H), 9.71 (s, 1H), 6.45 (d, 2H, J=11.2 Hz), 5.19 (d, J=8.0 Hz, 1H), 4.65 (s, 1H), 4.89-3.99 (m, 2H), 3.85-3.69 (m, 3H), 3.3-3.2 (m, 2H). LCMS: M/z: (M+1):350

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2.5 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto give a residue which
  5. customwas purified by column chromatography (silica gel, gradient MeOH in DCM)

Sources & evidence

ORD record
ord-b65135de0b4f4a28a239d3eca10386f9
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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