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

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	Methyl 5'-amino-2'-methyl-1,1'-biphenyl-4-carboxylate	HCID 21090583	—
Reactant	Methyl 5'-(3-furoylamino)-2'-methyl-1,1'-biphenyl-4-carboxylate 3-Furoic acid	HCID 69203913	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Methyl 5'-(3-furoylamino)-2'-methyl-1,1'-biphenyl-4-carboxylate	HCID 69152621	58%

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07151118B2
Source dataset	uspto-grants-2006_12
ORD ID	ord-8264960b7b8248de97295f90db57df6b
Source note	uspto-grants-2006_12