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Diisopropylethylamine → HCID 24852186, compound

HRID 2245373
Notes
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Reaction equation

HRID 2245373 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 242088151-(5-fluoro-2-phenoxyphenyl)-N-methylmethanamineHCID 87462668HCID 87462668, compound

Product 1

HCID 24852186HCID 24852186, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent
HCID 6344
Dichloromethane
Solvent

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

  1. temperatureAfter cooling to room temperature
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes