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

HRID 1678455
Notes
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Reaction equation

HRID 1678455 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[C:16]([NH2:18])[CH:15]=[CH:14][C:13]=2[CH3:19])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[N:20]1([C:26]2[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.CN1CCOCC1.ON1C2C=CC=CC=2N=N1.Cl.CN(CCCN=C=N)C>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[C:16]([NH:18][C:30](=[O:31])[C:29]3[CH:28]=[CH:27][C:26]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:34][CH:33]=3)[CH:15]=[CH:14][C:13]=2[CH3:19])=[CH:10][CH:11]=1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 3452784-(Morpholin-4-yl)benzoic acidHCID 21899179Dimethylaminopropyl carbodiimide hydrochlorideHCID 598223355'-Amino-2'-methyl-biphenyl-4-carboxylic acid ethyl ester

Product 1

HCID 59822331
2'-Methyl-5'-(4-morpholin-4-yl-benzoylamino)-biphenyl-4-carboxylic acid ethyl ester
Yield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5′-Amino-2′-methyl-biphenyl-4-carboxylic acid ethyl ester (2.15 g), 4-morpholin-4-yl benzoic acid (1.27 g), N-methylmorpholine (2.05 ml), 1-hydroxybenzotriazole (826 mg) and 1-ethyl-3-(3-(dimethylaminopropyl)carbodiimide hydrochloride (1.17 g) in dry DMF (30 ml) was stirred at 20 C for 18 h. Then the DMF was evaporated and the residue partitioned between water and dichloromethane. The dried extracts were evaporated and the residue purified on silica gel. Elution with 1-2% methanol in dichloromethane gave a colourless solid (2.4 g)

Workup

  1. customThen the DMF was evaporated
  2. customthe residue partitioned between water and dichloromethane
  3. customThe dried extracts were evaporated
  4. customthe residue purified on silica gel
  5. washElution with 1-2% methanol in dichloromethane

Sources & evidence

ORD record
ord-962cae0f652648a7a3b2a7d6b16275ea
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08008303B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes