Potassium Carbonate → N-(1,2,3,4-Tetrahydroquinolin-7-yl)-6-phenylnicotinamide

HRID 494214Notes

Reaction equation

HRID 494214 reaction equation
[C:1]1([C:7]2[CH:31]=[CH:30][C:10]([C:11]([NH:13][C:14]3[CH:23]=[C:22]4[C:17]([CH2:18][CH2:19][CH2:20][N:21]4C(=O)C(F)(F)F)=[CH:16][CH:15]=3)=[O:12])=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+]>O.CO>[NH:21]1[C:22]2[C:17](=[CH:16][CH:15]=[C:14]([NH:13][C:11](=[O:12])[C:10]3[CH:30]=[CH:31][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:8][CH:9]=3)[CH:23]=2)[CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 576827076-Phenyl-N-(1-trifluoroacetyl-1,2,3,4-tetrahydroquinolin-7-yl)nicotinamide

Product 1

HCID 57682748N-(1,2,3,4-Tetrahydroquinolin-7-yl)-6-phenylnicotinamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

6-Phenyl-N-(1-trifluoroacetyl-1,2,3,4-tetrahydroquinolin-7-yl)nicotinamide (Example 25) (155 mg, 0.364 mmol) and potassium carbonate (252 mg, 1.82 mmol) in water (2 ml) and methanol (8 ml) was stirred at ambient temperature for 40 mins. The resulting suspension was filtered and the solid was washed with water then dried in vacuo to give the title compound as a white solid. 1H NMR (250 MHz, CDCl3) δ (ppm): 9.11 (m, 1H), 8.22 (dd, 1H), 8.03 (m, 2H), 7.82 (d, 1H), 7.75 (br, 1H), 7.48 (m, 3H), 7.06 (d, 1H), 6.91 (d, 1H), 6.62 (dd, 1H), 3.95 (br, 1H), 3.30 (m, 2H), 2.73 (t, 2H), 1.93 (m, 2H).

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe solid was washed with water
  3. customthen dried in vacuo

Sources & evidence

ORD record
ord-ba67089d2a854d97bb45aa48367a348d
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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