WO2010057795 Alkylcyclohexylethers of dihydrotetraazabenzoazulenes

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Biological target:

Vasopressin: V1a

Activity:

Antagonist

Steps Conditions Reactions
a

SOCl2 / Et3N / DCM

Chlorination
b

Glycine ethyl ether / Et3N / EtOH

Secondary amine subtitution (nucleophilic substitution)
c Boc2O / DMAP / DCM  Boc protection 
d H2 / ZnBr2 / Pd-C / AcOEt Primary amine synthesis (nitro reduction)  
e t-BuOK / THF  Lactame synthesis 
f Lawesson reagent  /THF  Thioamide synthesis
Steps Conditions Reactions
a

TMSCl / imidazole / DMF

TMS synthesis
b

1. TMSOTf / DCM

2. Et3SiH / DCM

Ether synthesis
c Chiral separation   
Steps Conditions Reactions
a

H2 / Pd-C / AcOH

O-Benzyl deprotection
b

TsCl / Et3N / DMAP / DCM

Tosyl synthesis
c t-BuOK / Toluene  Cyclisation 
Steps Conditions Reactions
a

1. NaH / DMF

2. CS2

3. CH3-I / DMF


b

NBS / HF-pyridine / DCM

CF3 synthesis
Steps Conditions Reactions
a

Boc2O / MgClO4 / DCM

Terbutyl ether synthesis
Steps Conditions Reactions
a

NH2-NH2 / n-BuOH

Hydrazone synthesis
b

NaOH aq / dioxane

Carboxylic acid synthesis (Ester hydrolysis)
c

1. Ethyl chloroformate / Et3N / THF

2. NH2-NH2 / MeOH 

Hydrazone synthesis
Steps Conditions Reactions
a

n-butanol

Cyclisation

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