WO2010061329 3-aminocyclopentanecarboxamides as chemokine receptor modulators
Scaffold:3-aminocyclopentanecarboxamide
| Steps | Conditions | Reactions |
| a | Ethyl iodide / LDA / THF | Nucleophilic substitution |
| b | NaOH 2.5N / MeOH | Carboxylic acid synthesis (ester hydrolysis) |
| c | (1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane / BOP / DIEA / DMF | Amide synthesis (BOP coupling) |
| d | Hydroxylamine / H2O / MeOH | Amine deprotection (pyrrole group) |
| e | H2 / Pd-C / MeOH | Alkene reduction |
| f | Sodium acetoxyborohydride / DCM | Primary amine synthesis (Amination reductive) |
| g | HCl 4N / Dioxane | Boc deprotection |
| h | DMSO | Tertiary amine synthesis (Nucleophilic substitution) |
| Steps | Conditions | Reactions |
| a |
1. NaOH 2.5N / MeOH 2.BnOH / EDCI / DMAP / DCM |
Hydrolysis / Ester synthesis |
| b |
LDA / THF |
Nucleophilic substitution |
| c |
Hydroxylamine / MeOH |
Amine deprotection (Pyrrole deprotection) |
| d |
Sodium triacetoxyborohydride / DCM |
Secondary amine synthesis (Amination reductive) |
| e | trifluoroacetic anhydride / DIEA / DCM | COCF3 protection |
| f | Acetyl chloride / DIEA / DMAP / DCM | Acetyl synthesis |
| g | H2 / Pt-C / Pd-C / AcOH | Alkene reduction / O-Benzyl deprotection |
| h |
1. Oxalyl chloride / DCM 2. DIEA / DCM |
Amide synthesis |
| i |
1.K2CO3 / MeOH 2.NaBH4 / EtOH 3. HCl 4N / Dioxane |
Acetyl deprotection / COCF3 deprotection / Boc deprotection |
| Steps | Conditions | Reactions |
| a | DAST / DCM | Fluorination |