HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → HCID 66739331, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Dimethyl Sulfate | HCID 6497 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 46852135 | HCID 46852135 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Ammonia | HCID 222 | — |
| Product | HCID 66739331 | HCID 66739331 | 50.6% |
Reaction Steps
To a stirred solution of 2-({3-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-1-yl}carbonyl)-1H-benzimidazole (170 mg, 0.45 mmol) in THF (10 ml) was added NaOH (1.12 ml of a 2.5 M aqueous solution, 2.8 mmol). After 5 minutes, dimethylsulfate (0.2 ml, 2.1 mmol) was added and the reaction was stirred at room temperature for 16 hours. The reaction was then concentrated at reduced pressure and purified directly via FCC (using a gradient of eluents; 98:2 to 95:5 DCM:2M NH3 in MeOH) to give the title compound (45 mg, 25% yield) as yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08912176B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-4d9afbb74bf64c7d8a62442ac7efea7d |
| Source note | uspto-grants-2014_12 |