Triethylamine → HCID 69144872, compound

HRID 2223906Notes

Reaction equation

HRID 2223906 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:40]([O:49][CH3:50])(=[O:48])[C:41]1[C:42](=[CH:44][CH:45]=[CH:46][CH:47]=1)[NH2:43].C(N(CC)CC)C>ClCCl.CN(C)C=O>[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]([NH:43][C:42]4[CH:44]=[CH:45][CH:46]=[CH:47][C:41]=4[C:40]([O:49][CH3:50])=[O:48])=[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

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8635Methyl AnthranilateHCID 65578Oxalyl chlorideHCID 10275841HCID 10275841, compound

Product 1

HCID 69144872HCID 69144872, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [1-[2-[4-[N-(p-tolyl)-2-furancarboxamido]piperidin-1-yl]ethyl]cyclohexyl]acetic acid (synthesized in Preparation Example 3B-1) (678 mg) in dichloromethane (15 mL) was added N,N-dimethylformamide (2 drops) dropwise. Oxalyl chloride (228 mg) was then added to the solution under ice cooling. The solution was stirred under ice cooling for 2 hours. A 5-mL aliquot of the reaction solution was taken and was added to a solution of methyl anthranilate (99 mg) and triethylamine (182 mg) in dichloromethane (15 mL) dropwise under ice cooling. The reaction solution was stirred for 18 hours while the temperature was allowed to rise to room temperature. NH Silica gel was then added to the reaction solution, and it was concentrated under reduced pressure. The residue was purified by chromatography [silica gel, chloroform-methanol (20:1)] to give methyl 2-[2-[1-[2-[4-[N-(p-tolyl)-2-furancarboxamido]piperidin-1-yl]ethyl]cyclohexyl]acetylamino]benzoate (150 mg).

Workup

  1. stirringThe reaction solution was stirred for 18 hours while the temperature
  2. customto rise to room temperature
  3. additionNH Silica gel was then added to the reaction solution, and it
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue was purified by chromatography [silica gel, chloroform-methanol (20:1)]

Sources & evidence

ORD record
ord-ade023337386455ba75b3a7c21a7735d
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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