Triethylamine → HCID 59294513, compound

HRID 1877383Notes

Reaction equation

HRID 1877383 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:3]=1[O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O.[F:19][C:20]1[CH:21]=[C:22]([CH3:30])[CH:23]=[C:24]2[C:29]=1[NH:28][CH2:27][CH2:26][CH2:25]2.C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C>ClCCl>[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:3]=1[O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([N:28]1[C:29]2[C:24](=[CH:23][C:22]([CH3:30])=[CH:21][C:20]=2[F:19])[CH2:25][CH2:26][CH2:27]1)=[O:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 167927318-fluoro-6-methyl-1,2,3,4-tetrahydroquinolineHCID 29042269HCID 29042269, compound

Product 1

HCID 59294513HCID 59294513, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,5-dichloro-phenoxy)-benzoic acid (51.0 mg, 0.18 mmol, 1.0 equiv; Example 110, Step 1) in dichloromethane (2 mL) was added 8-fluoro-6-methyl-1,2,3,4-tetrahydro-quinoline (35.7 mg, 0.22 mmol, 1.2 equiv; [CAS RN 954260-80-1]), triethylamine (36.5 mg, 50 μL, 0.36 mmol, 2.0 equiv; [CAS RN 121-44-8]) and 2-chloro-1-methylpyridinium iodide (57.8 mg, 0.22 mmol, 1.2 equiv; [CAS RN 14338-32-0]). The reaction mixture was stirred at rt for 2 h. Removal of the solvent mixture under reduced pressure and purification by preparative HPLC on reversed phase (Xterra® PrepMSC 18, 5 μm, 19×50 mm column equipped with a Gilson Liquid Handler 215 autosampler, two Rainin Dynamax® SD-300 pumps, a Sedex ELSD 75 lightscatter and a Dionex UVD 340S UV detector) eluting with a gradient of acetonitrile/water provided 20.7 mg (27%) of the title compound. MS (ISP): 430.2 [M+H]+.

Workup

  1. customRemoval of the solvent mixture
  2. customunder reduced pressure and purification by preparative HPLC on reversed phase (Xterra® PrepMSC 18, 5 μm, 19×50 mm column
  3. customequipped with a Gilson Liquid Handler 215 autosampler, two Rainin Dynamax® SD-300 pumps
  4. washa Sedex ELSD 75 lightscatter and a Dionex UVD 340S UV detector) eluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-a586d28d37df4a168698994a0f3b3fb8
Source dataset
uspto-grants-2012_11
Patent number
US08309734B2

Reaction notes

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