Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Acetylpyridine | HCID 14286 | — |
| Reactant | 4-(Bromomethyl)benzonitrile | HCID 86996 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | Ether hydrochloride | HCID 10953452 | — |
| Reactant | tert-butyl N-{2-[(2-{[(tert-butoxy)carbonyl]amino}ethyl)amino]ethyl}carbamate | HCID 15157893 | — |
| Reactant | Bis(2-tert-butoxycarbonylaminoethyl)amino-4-methylphenylcyanide | HCID 69032449 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Hydrochloric Acid | HCID 313 | — |
| Product | 2-Pyridinecarboxaldehyde | HCID 14273 | — |
| Product | Sodium borohydride | HCID 4311764 | — |
Reaction Steps
A mixture of bis(2-tert-butoxycarbonylaminoethyl)amine (0.01 mol), 4-cyanobenzyl-bromide (0.01 mol), K2CO3 (0.05 mol), and CH3CN (70 mL) was heated at 60° C. for 10 hours. The resultant bis(2-tert-butoxycarbonylaminoethyl)amino-4-methylphenylcyanide was deprotected using HCl/ether, condensed with 2-acetyl pyridine (0.01 mol) in MeOH, and then reduced by NaBH4. After sequential treatments with pyridine-2-carboxaldehyde, NaBH4, and HCl, compound 110 was obtained in 75% overall yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07399776B2 |
|---|
| Source dataset | uspto-grants-2008_07 |
|---|
| ORD ID | ord-ae2070517a354cba97e0af6f6803cd24 |
|---|
| Source note | uspto-grants-2008_07 |
|---|
