Triethylamine → (S)-N-(3-pyridyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetamide hydrochloride

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	3-Aminopyridine	HCID 10009	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	2-((9S)-7-(4-chlorophenyl)-4,5,13-trimethyl-3-thia-1,8,11,12-tetraazatricyclo(8.3.0.0,2,6)trideca-2(6),4,7,10,12-pentaen-9-yl)acetic acid	HCID 66828107	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(S)-N-(3-pyridyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetamide hydrochloride	HCID 68971820	52.1%

Reaction Steps

(S)-(4-Chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f]-[1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetic acid (2.64 g) is dissolved in dimethylformamide (30 ml). N-Dimethylaminopropyl-N'-ethylcarbodiimide hydrochloride (1.51 g) and triethylamine (1.08 ml) are added in order and the mixture is stirred. Five minutes later, 3-aminopyridine (0.66 g) is added to the reaction mixture and the mixture is stirred at room temperature overnight. The reaction mixture is poured into water, and the obtained crystals are purified by column chromatography (chloroform: methanol =50: 1). The crystals are converted to hydrochloride with ethanol/hydrochloric acid in ethyl acetate, and recrystallized from ethanol/ethyl acetate to give 0.88 g of (S)-N-(3-pyridyl)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetamide hydrochloride, melting point 198°-201° C.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05712274
Source dataset	uspto-grants-1998_01
ORD ID	ord-978999084ac34d5d9bb2ea0de67d2ed0
Source note	uspto-grants-1998_01