Triethylamine → HCID 10208666, compound

HRID 2223907Notes

Reaction equation

HRID 2223907 reaction equation
[C:1]1([CH3:33])[CH:6]=[CH:5][C:4]([N:7]([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]3([CH2:29][C:30](O)=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:17][CH2:16]2)[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)=[O:9])=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[NH2:47][C:48]1[CH:53]=[N:52][CH:51]=[CH:50][N:49]=1>ClCCl.CN(C)C=O>[N:49]1[CH:50]=[CH:51][N:52]=[CH:53][C:48]=1[NH:47][C:30]([CH2:29][C:23]1([CH2:22][CH2:21][N:18]2[CH2:19][CH2:20][CH:15]([N:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:33])=[CH:2][CH:3]=3)[C:8]([C:10]3[O:11][CH:12]=[CH:13][CH:14]=3)=[O:9])[CH2:16][CH2:17]2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1)=[O:31]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 78747AminopyrazineHCID 10275841HCID 10275841, compound

Product 1

HCID 10208666HCID 10208666, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of [1-[2-[4-[N-(p-tolyl)-2-furancarboxamido]piperidin-1-yl]ethyl]cyclohexyl]acetic acid (synthesized in Example 3B-1) (201 mg) dissolved in dichloromethane (6 mL) was added N,N-dimethylformamide (2 drops). Oxalyl chloride (0.060 mL) was then added to the solution dropwise under ice cooling. The solution was stirred for 1.5 hours. After addition of triethylamine (0.12 mL) at that temperature, the solution was stirred for 20 minutes. 2-Aminopyrazine (128 mg) was then added to the solution and it was stirred at that temperature. The temperature was allowed to rise to room temperature and the solution was stirred for 16 hours. NH Silica gel was added to the reaction solution, and it was concentrated under reduced pressure. The resulting residue was purified by chromatography [at the first stage; NH silica gel, hexane-ethyl acetate (2:1) and at the second stage; silica gel, chloroform-methanol (10:1)] to give the title compound (116 mg).

Workup

  1. stirringthe solution was stirred for 20 minutes
  2. stirringwas stirred at that temperature
  3. customto rise to room temperature
  4. stirringthe solution was stirred for 16 hours
  5. additionNH Silica gel was added to the reaction solution, and it
  6. concentrationwas concentrated under reduced pressure
  7. customThe resulting residue was purified by chromatography [at the first stage

Sources & evidence

ORD record
ord-c6f2b9f80cb441a3b590e546929ac464
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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