Triethylamine → 2'-Methyl-5'-[(morpholine-4-carbonyl)-amino]-biphenyl-4-carboxylic acid ethyl ester

HRID 1678469Notes

Reaction equation

HRID 1678469 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].C(N(CC)CC)C.[N:27]1([C:33](Cl)=[O:34])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>C1COCC1>[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:33]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[O:34])[CH:15]=[CH:14][C:13]=2[CH3:19])=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 598223355'-Amino-2'-methyl-biphenyl-4-carboxylic acid ethyl ester

Product 1

HCID 598223402'-Methyl-5'-[(morpholine-4-carbonyl)-amino]-biphenyl-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 5′-amino-2′-methyl-biphenyl-4-carboxylic acid ethyl ester (520 mg) in dry THF (25 ml) containing triethylamine (0.57 ml) was treated with 4-morpholine-carbonyl chloride (0.26 ml). After 18 h. the mixture was partitioned between water and dichloromethane. The dried extracts were evaporated and the residue purified on silica gel. Elution with ethyl acetate:petrol 1:1 gave the title compound as a yellow oil (416 mg).

Workup

  1. customAfter 18 h. the mixture was partitioned between water and dichloromethane
  2. customThe dried extracts were evaporated
  3. customthe residue purified on silica gel
  4. washElution with ethyl acetate:petrol 1:1

Sources & evidence

ORD record
ord-70dd03b86b9f43ec921018c54d5d336f
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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