Diisopropylethylamine → Methyl 5'-(3-furoylamino)-2'-methyl-1,1'-biphenyl-4-carboxylate

HRID 859799Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 859799
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[CH:2]1.O1C=CC(C([NH:16][C:17]2[CH:18]=[CH:19][C:20]([CH3:33])=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=3)[CH:22]=2)=O)=C1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.NC1C=CC(C)=C(C2C=CC(C(OC)=O)=CC=2)C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[O:1]1[CH:5]=[CH:4][C:3]([C:6]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([CH3:33])=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=3)[CH:22]=2)=[O:8])=[CH:2]1

Komponenten

7

Edukt 5

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21090583Methyl 5'-amino-2'-methyl-1,1'-biphenyl-4-carboxylateHCID 69203913Methyl 5'-(3-furoylamino)-2'-methyl-1,1'-biphenyl-4-carboxylate 3-Furoic acid

Produkt 1

HCID 69152621Methyl 5'-(3-furoylamino)-2'-methyl-1,1'-biphenyl-4-carboxylateAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl 5′-(3-furoylamino)-2′-methyl-1,1′-biphenyl-4-carboxylate 3-Furoic acid (557 mg, 4.97 mmol), HATU (1.89 g, 4.97 mmol), HBTU (560 mg, 4.14 mmol), methyl 5′-amino-2′-methyl-1,1′-biphenyl-4-carboxylate (1.0 g, 4.14 mmol) and DIPEA (2.17 ml, 12.43 mmol) were mixed in DMF (5 ml) and the reaction stirred at room temperature for 18 h. The DMF was evaporated under vacuum, the residue partitioned between DCM (50 ml) and aqueous sodium carbonate (1M, 50 ml) and the aqueous extracted with DCM (2×30 ml). The combined organics were washed with brine (75 ml), dried (magnesium sulphate) and concentrated under vacuum. The residue was purified on a silica flash column eluting with DCM/ethanol/ammonia (500:8:1), which after evaporation of the solvents under vacuum gave methyl 5′-(3-furoylamino)-2′-methyl-1,1′-biphenyl-4-carboxylate (800 mg, 58%). LCMS: retention time 3.41 min, MH+336.

Aufarbeitung

  1. customThe DMF was evaporated under vacuum
  2. customthe residue partitioned between DCM (50 ml) and aqueous sodium carbonate (1M, 50 ml)
  3. extractionthe aqueous extracted with DCM (2×30 ml)
  4. washThe combined organics were washed with brine (75 ml)
  5. dry with materialdried (magnesium sulphate)
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified on a silica flash column
  8. washeluting with DCM/ethanol/ammonia (500:8:1), which
  9. customafter evaporation of the solvents under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8264960b7b8248de97295f90db57df6b
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07151118B2

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