Triethylamine → HCID 11296120, compound

HRID 2104509Notes

Reaction equation

HRID 2104509 reaction equation
Cl[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH2:14][C:15]1[CH:16]=[C:17]([C:21]2[C:30]3[C:25](=[C:26]([C:31]([F:34])([F:33])[F:32])[CH:27]=[CH:28][CH:29]=3)[N:24]=[CH:23][C:22]=2[C:35]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:36])[CH:18]=[CH:19][CH:20]=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[C:35]([C:22]1[CH:23]=[N:24][C:25]2[C:30]([C:21]=1[C:17]1[CH:16]=[C:15]([NH:14][S:2]([C:5]3[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=3)(=[O:4])=[O:3])[CH:20]=[CH:19][CH:18]=1)=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:34])([F:32])[F:33])(=[O:36])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 823854-(Chlorosulfonyl)benzoic acidHCID 11326798[4-(3-Aminophenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)Methanone

Product 1

HCID 11296120HCID 11296120, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-(Chlorosulfonyl)benzoic acid (0.11 g, 0.5 mmol) in 5 mL of THF was added dropwise to a stirred solution of [4-(3-aminophenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone (0.098 g, 0.25 mmol) and triethylamine (0.4 mL, 0.29 mmol) in 5 mL of THF at room temperature. The reaction mixture was stirred overnight, diluted with ethyl acetate, washed with water, and concentrated. The residue was purified by semi-preparative HPLC (Column: Phenomenex C18 Luna 21.6 mm×60 mm, 50M; Solvent A: Water (0.1% TFA buffer); Solvent B: Acetonitrile (0.1% TFA buffer); Solvent Gradient: Time 0: 0% B; 10 min: 100% B; Hold 100% B 5 min. Flow Rate: 22.5 mL/min). The product was collected based on UV absorption and concentrated to give the title compound as a brown solid (0.075 g, 50%): MS (EI) m/z 601.1 (M+H)+; 1H NMR (DMSO-d6): δ 7.03 (d, J=7.7 Hz, 1H), 7.33 (t, J=8.0 Hz, 1H), 7.39 (t, J=7.8 Hz, 2H), 7.56 (t, J=7.4 Hz, 1H), 7.60-8.75 (m, 9H), 8.06 (d, J=8.6 Hz, 1H), 8.36 (d, J=7.3 Hz, 1H), 9.16 (s, 1H), 10.34 (s, 1H).

Workup

  1. washwashed with water
  2. concentrationconcentrated
  3. customThe residue was purified by semi-preparative HPLC (Column: Phenomenex C18 Luna 21.6 mm×60 mm, 50M; Solvent A: Water (0.1% TFA buffer); Solvent B: Acetonitrile (0.1% TFA buffer); Solvent Gradient: Time 0: 0% B; 10 min: 100% B; Hold 100% B 5 min. Flow Rate: 22.5 mL/min)
  4. customThe product was collected
  5. custombased on UV absorption
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1b98e944abfa4ecaa49212adb4760527
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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