Dimethylformamide → HCID 18457803, compound

HRID 747564Notes

Reaction equation

HRID 747564 reaction equation
[CH3:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14](O)=[O:15])=[CH:10][CH:9]=2)=[CH:6][C:5]([C:17]([NH:19][CH2:20][CH2:21][CH3:22])=[O:18])=[CH:4][CH:3]=1.C(N(CC)CC)C.CS([N:34]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[N:36]=[N:35]1)(=O)=O.CN(C=O)C>C1COCC1>[N:34]1([C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]3[C:2]([CH3:1])=[CH:3][CH:4]=[C:5]([C:17]([NH:19][CH2:20][CH2:21][CH3:22])=[O:18])[CH:6]=3)=[CH:9][CH:10]=2)=[O:15])[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[N:36]=[N:35]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 7920441-(Methylsulfonyl)-1H-benzotriazoleHCID 18457823HCID 18457823, compound

Product 1

HCID 18457803HCID 18457803, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6′-Methyl-3′-[(propylamino)carbonyl]-1,1′-biphenyl-4-carboxylic acid (121 mg, 0.41 mmol), triethylamine (100 μl) and 1-(methylsulphonyl)-1H-benzotriazole (119 mg, 0.6 mmol) were mixed in THF (3 ml) and DMF (0.5 ml) and heated at reflux for 3 h. The reaction was concentrated under vacuum and partitioned between chloroform (5 ml) and water (5 ml). The aqueous was washed with chloroform (3 ml) and the combined organics reduced to dryness under vacuum. The residue was chromatographed on an SPE (silica, 5 g) eluting with chloroform, ether and ethylacetate, which after evaporation of the solvent under vacuum gave 4′-[(1H-1,2,3benzotriazol-1-yl)carbonyl]-6-methyl-N-propyl-1,1′-biphenyl-3-carboxamide (150 mg).

Workup

  1. temperatureat reflux for 3 h
  2. concentrationThe reaction was concentrated under vacuum
  3. custompartitioned between chloroform (5 ml) and water (5 ml)
  4. washThe aqueous was washed with chloroform (3 ml)
  5. customThe residue was chromatographed on an SPE (silica, 5 g)
  6. washeluting with chloroform, ether and ethylacetate, which
  7. customafter evaporation of the solvent under vacuum

Sources & evidence

ORD record
ord-115a844b4cc64ba7b6e73051ee26515a
Source dataset
uspto-grants-2008_07
Patent number
US07396843B2

Reaction notes

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