Triethylamine → HCID 71548369, compound

HRID 1184572Notes

Reaction equation

HRID 1184572 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C@H:9]2[CH2:17][N:12]3[CH2:13][CH2:14][NH:15][CH2:16][C@@H:11]3[CH2:10]2)=[N:6][CH:7]=1.C(N(CC)CC)C.[F:25][C:26]([F:36])([F:35])[C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30]Cl>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C@H:9]2[CH2:17][N:12]3[CH2:13][CH2:14][N:15]([CH2:30][C:29]4[CH:32]=[CH:33][CH:34]=[C:27]([C:26]([F:25])([F:35])[F:36])[CH:28]=4)[CH2:16][C@@H:11]3[CH2:10]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 697163-(Trifluoromethyl)benzyl chlorideHCID 71547981HCID 71547981, compound

Product 1

HCID 71548369HCID 71548369, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of Example 57 (76.2 mg, 0.3 mmol) and triethylamine (61 mg, 0.6 mmol) in dichloromethane (2 mL) was added 3-(trifluoromethyl)benzyl chloride (93 mg, 0.48 mmol). The mixture was stirred at 50° C. for 8 hours and then concentrated. The residue was purified by chromatography on silica gel (ethyl acetate/methanol=10:1) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.80 (m, 3H), 2.16-2.26 (m, 3H), 2.38 (m, 1H), 2.70 (m, 1H), 2.86 (m, 2H), 3.60 (m, 3H), 5.24 (m, 1H), 6.83 (d, 1H, J=7 Hz), 7.60 (m, 4H), 7.80 (d, 1H, J=7 Hz), 8.18 (s, 1H), 8.40 (s, 1H); MS (ESI) m/z 412 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by chromatography on silica gel (ethyl acetate/methanol=10:1)

Sources & evidence

ORD record
ord-95996e76f7654f7b8fcf4062db350120
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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