Triethylamine → HCID 71548072, compound

HRID 1184566Notes

Reaction equation

HRID 1184566 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:37])([F:36])[C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30](Cl)=[O:31]>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]([C:30]([C:29]4[CH:33]=[CH:34][CH:35]=[C:27]([C:26]([F:25])([F:36])[F:37])[CH:28]=4)=[O:31])[CH2:16][C@@H:11]3[CH2:10]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 71547981HCID 71547981, compound

Product 1

HCID 71548072HCID 71548072, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 57 (50.7 mg, 0.2 mmol) and triethylamine (40 mg, 0.4 mmol) in dichloromethane (1 mL) was added 3-(trifluoromethyl)benzoyl chloride (50 mg, 0.24 mmol). The mixture was stirred at room temperature for 3 hours. The residue was purified by chromatography on silica gel (ethyl acetate) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.70-1.92 (m, 2H), 2.16-2.27 (m, 3H), 2.52 (m, 1H), 2.82-3.25 (m, 2H), 3.60 (m, 2H), 4.45-4.62 (m, 1H), 5.28 (m, 1H), 6.83 (m, 1H), 7.75 (m, 5H), 8.20 (s, 1H); MS (ESI) m/z 426 (M+H)+.

Workup

  1. customThe residue was purified by chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-008c4eeea65f4ecd85ccd3be06b88421
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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