3-(Trifluoromethyl)benzoyl chloride → HCID 59833820, compound

HRID 270703Notes

Reaction equation

HRID 270703 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:19])=[C:6]([C:8]2[C:9](=[O:18])[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[CH:13][CH:12]=3)[CH:7]=1.CCN(C(C)C)C(C)C.[F:29][C:30]([F:41])([F:40])[C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34](Cl)=[O:35]>C1COCC1.CCOC(C)=O>[Cl:19][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:34](=[O:35])[C:33]2[CH:37]=[CH:38][CH:39]=[C:31]([C:30]([F:29])([F:40])[F:41])[CH:32]=2)=[CH:7][C:6]=1[C:8]1[C:9](=[O:18])[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][N:14]=[CH:13][CH:12]=2

Participants

6

Reactant 3

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 81531DiisopropylethylamineHCID 69292328HCID 69292328, compound

Product 1

HCID 59833820HCID 59833820, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(5-amino-2-chloro-phenyl)-1H-[1,6]-naphthyridin-2-one (60 mg, 0.23 mmol) and DIPEA (82 μl, 0.46 mmol) in anhydrous THF (2.5 mL), is added a solution of 3-trifluoromethyl-benzoyl chloride (44 μl). This mixture is stirred for 30 minutes at room temperature, diluted with EtOAc (50 mL), washed with water (10 mL) and brine (10 mL), dried over MgSO4, concentrated and purified by preparative HPLC, to give N-[4-chloro-3-(2-oxo-1,2-dihydro-[1,6]naphthyridin-3-yl)-phenyl]-3-trifluoromethyl-benzamide (18.3 mg).

Workup

  1. washwashed with water (10 mL) and brine (10 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-9ed09b80befe4bfe83f9f8c09937937a
Source dataset
uspto-grants-2008_11
Patent number
US07449582B2

Reaction notes

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