Trifluoroacetic acid → HCID 10162803, compound

Participants

Role	Name	HCID	Charge
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	Triethylsilane	HCID 12052	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	(R)-7-Cyano-4-[[2-(dimethylamino)ethyl]sulfonyl]-2,3,4,5-tetrahydro-1-(5-oxazolylmethyl)-3-(phenylmethyl)-1H-1,4-benzodiazepine	HCID 10140618	—
Reactant	1,2-Oxazole-3-carbaldehyde	HCID 18373078	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 10162803	HCID 10162803	—

Reaction Steps

To a mixture of 3-formylisoxazole (19.4 mg, 0.2 mmol) and Compound B of Example 25 (39.9 mg, 0.1 mmol) in DCM (0.5 mL) at rt was added TFA (45 mg, 0.4 mmol), followed by triethylsilane (35 mg, 0.3 mmol). The resulting mixture was stirred at rt for 1 hour, neutrallized with NaHCO3 solution and extracted with DCM (2×5 mL). The combined extract was dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography (SiO2; ethyl acetate: methanol ammonia/100:10:0.1) to afford the title compound, 45 mg (87%). MS: m/e (M+H)+=480.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06458783B1
Source dataset	uspto-grants-2002_10
ORD ID	ord-b73c8993eebe46619d3c02a993624fe3
Source note	uspto-grants-2002_10