Triethylamine → HCID 53311618, compound

HRID 1025902Notes

Reaction equation

HRID 1025902 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[C:10]([C:11]([OH:13])=O)=[CH:9][N:8]=[CH:7][N:6]=1.[I-].ClC1C=CC=C[N+]=1C.C(N(CC)CC)C.[NH:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:38][CH2:37][CH2:36]1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:3]=1[O:4][C:5]1[C:10]([C:11]([N:35]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH2:38][CH2:37][CH2:36]2)=[O:13])=[CH:9][N:8]=[CH:7][N:6]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 694601,2,3,4-TetrahydroquinolineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 516892Sodium BicarbonateHCID 673202614-(2,5-Dichloro-phenoxy)-pyrimidine-5-carboxylic acid

Product 1

HCID 53311618HCID 53311618, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 200 mg (0.7 mmol) 4-(2,5-dichloro-phenoxy)-pyrimidine-5-carboxylic acid in 2 mL dichloromethane were added 197 mg (0.77 mmol) 2-chloro-1-methylpyridinium iodide (commercially available, CAS RN 14338-32-0), 0.2 mL (1.4 mmol) triethylamine and 103 mg (0.77 mmol) 1,2,3,4-tetrahydroquinoline (commercially available, CAS RN 635-46-1). The solution was stirred 2 hours at room temperature. The reaction mixture was poured on saturated aqueous sodium bicarbonate solution and extracted three times with dichloromethane. The combined organic layers were dried over magnesium sulfate and concentrated under vacuum. The residue was purified by preparative HPLC (Phenomenex Gemini column) using a gradient of acetonitrile:water (containing 0.05% formic acid) (10:90 to 98:2) to give 5.6 mg (2%) of the desired compound. MS (ESI): m/z=400.2 [M+H]+.

Workup

  1. extractionextracted three times with dichloromethane
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by preparative HPLC (Phenomenex Gemini column)

Sources & evidence

ORD record
ord-d8ec0e8fc8444cdb88693c93b84f2b27
Source dataset
uspto-grants-2014_05
Patent number
US08729091B2

Reaction notes

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