Diisopropylethylamine → HCID 24852186, compound

HRID 2245373Notes

Reaction equation

[I-].C[N+]1C=C[N:5]([C:8](=[O:30])/[N:9]=[C:10]2\[S:11][C:12]([CH3:29])=[CH:13][N:14]\2[C:15]2[CH:28]=[CH:27][C:18]3[O:19][C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[O:22][C:17]=3[CH:16]=2)[CH:4]=1.[F:31][C:32]1[CH:33]=[CH:34][C:35]([O:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[C:36](CNC)[CH:37]=1.[CH3:48]CN(C(C)C)C(C)C>C(#N)C.C(Cl)Cl>[F:31][C:32]1[CH:33]=[CH:34][C:35]([O:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[C:36]([CH:37]=1)[CH2:4][N:5]([CH3:48])[C:8](/[N:9]=[C:10]1\[S:11][C:12]([CH3:29])=[CH:13][N:14]\1[C:15]1[CH:28]=[CH:27][C:18]2[O:19][C:20]([F:26])([F:25])[C:21]([F:23])([F:24])[O:22][C:17]=2[CH:16]=1)=[O:30]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of Example 81A (0.1 g, 0.18 mmol) and 1-(5-fluoro-2-phenoxyphenyl)-N-methylmethanamine (0.20 mmol) in anhydrous acetonitrile (3 mL) was added Hunig's base (0.025 g), and the solution was heated at 60° C. for 3 hours. After cooling to room temperature, the reaction mixture was diluted with 50 mL of CH2Cl2 and washed with water and brine, dried over sodium sulfate, and concentrated under reduced pressure. The crude residue was choromatographed over silica using CH2Cl2 to give the titled compound. 1H NMR (CD3OD) δ ppm 2.25 (3H), 2.90 (3H), 4.60 (2H), 6.90-7.60 (12H); MS (ESI) 578 (M+H)+.

Workup

temperatureAfter cooling to room temperature
washwashed with water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-759e28dde36d48cb8b482caa8984dd23
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683084B2

Reaction notes

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