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

HRID 1678534Notes

Reaction equation

HRID 1678534 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].[F:22][C:23]1[CH:24]=C(N)[CH:26]=[CH:27][C:28]=1[N:29]1CCOCC1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:57][N:58]1[CH2:63][CH2:62][O:61][CH2:60][CH2:59]1>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:29][C:28]3[CH:27]=[CH:26][C:57]([N:58]4[CH2:63][CH2:62][O:61][CH2:60][CH2:59]4)=[CH:24][C:23]=3[F:22])[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 757711-HydroxybenzotriazoleHCID 14853303-Fluoro-4-morpholinoanilineHCID 532278844-Chloro-3-(4-ethoxycarbonylphenyl)benzoic acid

Product 1

HCID 673712232'-Chloro-5'-(2-fluoro-4-morpholin-4-yl-phenylcarbamoyl)-biphenyl-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-chloro-biphenyl-3,4′-dicarboxylic acid 4′-ethyl ester (213 mg), 3-fluoro-4-morpholin-4-yl-phenylamine (179 mg), EDAC (174 mg), HOBT (123 mg) and N-methylmorpholine (200 μl) in DMF (3 ml) was stirred at room temperature. After 11 h, water (30 ml) was added and the resulting suspension filtered. The residue was then purified by chromatography. Elution with 1:1 ethyl acetate:petrol gave a brown oil (235 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-2a74595c25314e6dad8db0b72a887e34
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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