4-Methylmorpholine → 2'-Chloro-5'-(4-morpholin-4-yl-phenylcarbamoyl)-biphenyl-4-carboxylic acid ethyl ester

HRID 1678533Notes

Reaction equation

HRID 1678533 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[C:14]([C:19]([OH:21])=O)[CH:13]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[CH:25][CH:24]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[C:14]([C:19](=[O:21])[NH:22][C:23]3[CH:24]=[CH:25][C:26]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)=[CH:27][CH:28]=3)[CH:15]=[CH:16][C:17]=2[Cl:18])=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 757711-HydroxybenzotriazoleHCID 532278844-Chloro-3-(4-ethoxycarbonylphenyl)benzoic acid

Product 1

HCID 598223602'-Chloro-5'-(4-morpholin-4-yl-phenylcarbamoyl)-biphenyl-4-carboxylic acid ethyl esterYield 35.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-chloro-biphenyl-3,4′-dicarboxylic acid 4′-ethyl ester (800 mg), N-(4-aminophenyl)morpholine (469 mg), EDAC (504 mg), HOBT (355 mg) and N-methylmorpholine (578 μl) in DMF (10 ml) was stirred at room temperature. After 1 h, water (80 ml) was added and the resulting suspension filtered. The residue was then purified by chromatography. Elution with 1:1 ethyl acetate:petrol gave a yellow crystalline solid (437 mg).

Workup

  1. filtrationthe resulting suspension filtered
  2. customThe residue was then purified by chromatography
  3. washElution with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-9bcd9d97c1074522826b802369c66e15
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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