Acetyl chloride → N-(1-acetyl-1,2,3,4-tetrahydroquinolin-7-yl)-[1,1'-biphenyl]-4-carboxamide

HRID 494215Notes

Reaction equation

HRID 494215 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:16][CH:15]=3)=[O:13])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:33](Cl)(=[O:35])[CH3:34].C(O)C(N)(CO)CO.[N-]=C=O>C(Cl)Cl>[C:33]([N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)=[O:13])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1)(=[O:35])[CH3:34]

Participants

7

Reactant 5

HCID 6367Acetyl chlorideHCID 6503Tris(hydroxymethyl)aminomethaneHCID 8471TriethylamineHCID 105034IsocyanateHCID 44415452N-(1,2,3,4-Tetrahydroquinolin-7-yl)-1,1'-biphenyl-4-carboxamide

Product 1

HCID 7586175N-(1-acetyl-1,2,3,4-tetrahydroquinolin-7-yl)-[1,1'-biphenyl]-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(1,2,3,4-tetrahydroquinolin-7-yl)-1,1′-biphenyl-4-carboxamide (Example 24) (66 mg, 0.2 mmol) in DCM (1 ml) was added triethylamine (42 ul, 0.3 mmol) followed by acetyl chloride (20.5 ul, 0.3 mmol). The reaction was stirred at ambient temperature for 15 mins then treated with polymer supported trisamine resin (31 mg, 0.1 mmol) and polymer supported isocyanate resin (20 mg, 0.04 mmol). After 5 mins the resins were removed by filtration and the filtrate was washed with 2M hydrochloric acid, dried over MgSO4 and concentrated in vacuo to give the title compound as an off-white solid. 1H NMR (250 MHz, CDCl3) δ (ppm): 7.94 (d, 2H), 7.84 (d, 1H), 7.78 (br, 1H), 7.72 (d, 2H), 7.64 (d, 2H), 7.45 (m, 4H), 7.15 (d, 1H), 3.80 (t, 2H), 2.74 (t, 2H), 2.33 (s, 3H), 1.98 (qn, 2H).

Workup

  1. additionthen treated with polymer
  2. customAfter 5 mins the resins were removed by filtration
  3. washthe filtrate was washed with 2M hydrochloric acid
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-85bffcc316db44908da2fa3ee2039838
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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