Dichloromethane → ((S)-2-Azepan-1-yl-1-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-2-oxoethyl)-carbamic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Azepane	HCID 8119	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733286	—
Reactant	5-Chloro-thiophene-2-carboxylic acid [(S)-2-[2-ethyl-3-(3-oxo-morpholin-4-yl)-benzenesulfonylamino]-3-((S)-3-methyl-morpholin-4-yl)-3-oxo-propyl]-amide	HCID 44200855	—
Product	((S)-2-Azepan-1-yl-1-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-2-oxoethyl)-carbamic acid tert-butyl ester	HCID 67155359	—

Reaction Steps

To stirred intermediate 1 (1.5 g, 4.3 mmol) in 20 ml DCM was added azepane (426 mg, 4.3 mmol), TOTU (1.692 g, 5.16 mmol) and DIPEA (1.46 ml, 8.60 mmol). After 2 h the mixture was washed subsequently with sat. aq NaHCO3, and brine. The organic layer was dried with MgSO4, filtered and evaporated. The crude material (2.2 g) was used without further purification in the next step.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08378092B2
Source dataset	uspto-grants-2013_02
ORD ID	ord-a94ff4e10ded4d37a2f6c6b2fe70e83e
Source note	uspto-grants-2013_02