Triethylamine → HCID 89466155, compound

HRID 1184583Notes

Reaction equation

HRID 1184583 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C@H:9]2[C@@H:13]3[CH2:14][NH:15][CH2:16][CH2:17][N:12]3[CH2:11][CH2:10]2)=[N:6][CH:7]=1.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24].C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C@H:9]2[C@@H:13]3[CH2:14][N:15]([C:23]([C:22]4[CH:26]=[CH:27][CH:28]=[C:20]([C:19]([F:18])([F:29])[F:30])[CH:21]=4)=[O:24])[CH2:16][CH2:17][N:12]3[CH2:11][CH2:10]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 89466171HCID 89466171, compound

Product 1

HCID 89466155HCID 89466155, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 100F (120 mg, 0.473 mmol) and 3-(trifluoromethyl)benzoyl chloride (118 mg, 0.568 mmol) in dichloromethane (1.5 mL) was added triethylamine (0.3 mL, 2.18 mmol). The mixture was stirred at room temperature for 16 hours. The mixture was concentrated and purified via HPLC (Gilson®, Xbridge™ 30×100 mm column, eluted with pH=10 aqueous ammonium bicarbonate-ammonium hydroxide/methanol, UV=220 nm) to give the title compound 1H NMR (400 MHz, pyridine-4.90° C.) δ ppm 1.66-1.79 (m, 1 H), 2.18-2.44 (m, 4 H), 2.85-2.90 (m, 1 H), 2.92-3.13 (m, 3 H), 4.19 (br. s, 1 H), 4.58 (br. s, 1 H), 5.10-5.16 (m, 1 H), 6.64 (d, 1H, J=8 Hz), 7.40-7.50 (m, 2 H), 7.63-7.69 (m, 2 H), 7.87 (s, 1 H), 7.96 (s, 1 H); MS (DCI) m/z 426 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified via HPLC (Gilson®, Xbridge™ 30×100 mm column, eluted with pH=10 aqueous ammonium bicarbonate-ammonium hydroxide/methanol, UV=220 nm)

Sources & evidence

ORD record
ord-4d949baf200249d691fa1774167b6c97
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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