Triethylamine → Furan-2-carboxylic acid [2-methyl-3'-(4-morpholin-4-yl-phenylcarbamoyl)-biphenyl-4-yl]-amide

HRID 1678460Notes

Reaction equation

HRID 1678460 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[CH:17]=[C:18]([C:22]4[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][C:23]=4[CH3:29])[CH:19]=[CH:20][CH:21]=3)=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[O:37]1[CH:41]=[CH:40][CH:39]=[C:38]1[C:42](Cl)=[O:43]>CN(C=O)C>[CH3:29][C:23]1[CH:24]=[C:25]([NH:28][C:42]([C:38]2[O:37][CH:41]=[CH:40][CH:39]=2)=[O:43])[CH:26]=[CH:27][C:22]=1[C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:14](=[O:15])[NH:13][C:10]2[CH:9]=[CH:8][C:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[CH:12][CH:11]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 598223324'-Amino-2'-methyl-biphenyl-3-carboxylic acid (4-morpholin-4-yl-phenyl)-amide

Product 1

HCID 59822350Furan-2-carboxylic acid [2-methyl-3'-(4-morpholin-4-yl-phenylcarbamoyl)-biphenyl-4-yl]-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4′-amino-2′-methyl-biphenyl-3-carboxylic acid (4-morpholin-4-yl-phenyl)-amide (40 mg) and triethylamine (0.4 ml) in dry DMF (3 ml) was treated with furan-2-carbonyl chloride (0.015 ml) and the mixture stirred at 20 C for 18 h. The mixture was then partitioned between water and dichloromethane. The dried extract was then evaporated and the residue purified on silica gel. Elution with dichloromethane:ethanol:0.880 ammonia; 400:8:1 gave a colourless foam (46 mg).

Workup

  1. customThe mixture was then partitioned between water and dichloromethane
  2. extractionThe dried extract
  3. customwas then evaporated
  4. customthe residue purified on silica gel
  5. washElution with dichloromethane

Sources & evidence

ORD record
ord-ff18a3670f254a9188c057238b9529d7
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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