HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Methyl-2-imidazolecarboxaldehyde → (1h-Benzoimidazol-2-ylmethyl)-(4-{[(1-methyl-1h-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Methyl-2-imidazolecarboxaldehyde | HCID 139575 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | N-[(1H-Benzo[d]imidazol-2-yl)methyl]-N-(4-(aminomethyl)-benzyl)-5,6,7,8-tetrahydroquinolin-8-amine | HCID 21985008 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | (1h-Benzoimidazol-2-ylmethyl)-(4-{[(1-methyl-1h-imidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine | HCID 20763961 | 67.5% |
Reaction Steps
Using General Procedure B: A solution of 1-methyl-2-imidazole carboxaldehyde (27.5 mg, 0.25 mmol) and (4-aminomethyl-benzyl)-(1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (100 mg, 0.25 mmol) in MeOH (2.0 mL) was stirred overnight at room temperature. NaBH4 (37.5, 0.75 mmol) was added and the resultant mixture stirred for an additional 15 minutes. Purification of the crude white foam by column chromatography on silica gel (CH2Cl2[MeOH/NH4OH, 50:1:1) followed by radial chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 200:3:2) afforded the desired amine (83 mg, 67%) as a white foam.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07084155B2 |
| Source dataset | uspto-grants-2006_08 |
| ORD ID | ord-4a059695fa0041618a8dc164a748bfc6 |
| Source note | uspto-grants-2006_08 |