4-Methylmorpholine → 2'-Chloro-5'-[4-(4-methanesulfonyl-piperazin-1-ylmethyl)-phenylcarbamoyl]-biphenyl-4-carboxylic acid ethyl ester

HRID 1678535Notes

Reaction equation

HRID 1678535 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].[CH3:22][S:23]([N:26]1[CH2:31][CH2:30][N:29]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=2)[CH2:28][CH2:27]1)(=[O:25])=[O:24].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:39][C:36]3[CH:37]=[CH:38][C:33]([CH2:32][N:29]4[CH2:28][CH2:27][N:26]([S:23]([CH3:22])(=[O:25])=[O:24])[CH2:31][CH2:30]4)=[CH:34][CH:35]=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 757711-HydroxybenzotriazoleHCID 113692314-(4-Methanesulfonyl-piperazin-1-ylmethyl)-phenylamineHCID 532278844-Chloro-3-(4-ethoxycarbonylphenyl)benzoic acid

Product 1

HCID 673723822'-Chloro-5'-[4-(4-methanesulfonyl-piperazin-1-ylmethyl)-phenylcarbamoyl]-biphenyl-4-carboxylic acid ethyl esterYield 86.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-chloro-biphenyl-3,4′-dicarboxylic acid 4′-ethyl ester (152 mg), 4-(4-methanesulfonyl-piperazin-1-ylmethyl)-phenylamine (175 mg), EDAC (125 mg), HOBT (88 mg) and N-methylmorpholine (143 μl) in DMF (3 ml) was stirred at room temperature. After 1 h, water (30 ml) was added and the resulting suspension filtered. The residue was then purified by chromatography. Gradient elution with 30-100% ethyl acetate in petrol gave a beige solid (240 mg).

Workup

  1. filtrationthe resulting suspension filtered
  2. customThe residue was then purified by chromatography
  3. washGradient elution with 30-100% ethyl acetate in petrol

Sources & evidence

ORD record
ord-2c822a64b725487aa99b53d73ee62db1
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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