2-(Trifluoromethyl)benzoyl chloride → HCID 178519517, compound

HRID 882804Notes

Reaction equation

HRID 882804 reaction equation
[N:1]1([CH2:8][C:9]2[NH:20][C:19]3[C:21]4[C:15]([C:16](=[O:22])[NH:17][N:18]=3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27](Cl)=[O:28]>C(Cl)Cl>[F:23][C:24]([F:34])([F:35])[C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([N:4]1[CH2:5][CH2:6][CH2:7][N:1]([CH2:8][C:9]2[NH:20][C:19]3[C:21]4[C:15]([C:16](=[O:22])[NH:17][N:18]=3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH2:2][CH2:3]1)=[O:28]

Participants

4

Reactant 2

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 178518773HCID 178518773, compound2×

Product 1

HCID 178519517HCID 178519517, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Synthesized from compound 26. To a solution of compound 26 (0.2 g, 0.6 mmol) in 5 mL of CH2Cl2 was added 1 mmol of TEA and 0.8 mmol of 2-trifluoromethyl-benzoyl chloride. The reaction was stirred overnight at room temperature. After the solvents were evaporated, the residue was purified with semi-preparative HPLC to afford a solid (15% yield). MP: 140-142° C.; MS (ES−): 469; 1H NMR (400 MHz, CDCl3): 1.92-2.10 (m, 2H), 2.91-3.10 (m, 4H), 3.36-3.44 (m, 2H), 3.64-3.74 (m, 2H), 3.93 (m, 2H), 7.38 (m, 1H), 7.57 (m, 3H), 7.79 (m, 2H), 7.93 (m, 1H). Anal. Calcd. for C23H21F3N6O2.0.9HCl: C, 54.89; H, 4.39; N, 16.70; Found: C, 54.93; H, 4.43; N, 16.34.

Workup

  1. customAfter the solvents were evaporated
  2. customthe residue was purified with semi-preparative HPLC

Sources & evidence

ORD record
ord-731d0d27cc5d45a68d808db2b2aa482f
Source dataset
uspto-grants-2012_08
Patent number
US08236802B2

Reaction notes

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