Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 2-Chlorobenzothiazole | HCID 11987 | — |
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Product | HCID 58548512 | HCID 58548512 | 73% |
Reaction Steps
A mixture of (1S,3S)-3-aminocyclobutanol hydrochloride (120 mg, 0.98 mmol, 1.0 eqv), 2-chloro-benzothiazole (purchased from ALDRICH™) (169 mg, 1 mmol, 1.02 eqv) and DIEA (286 mg, 2 mmol, 2.04 eqv) in NMP (2 mL) was heated to 180° C. for 2 hours in microwave. To the reaction mixture was added water, and the residue was extracted with EtOAc (30 mL). The combined organic layer was washed with brine and dried over Na2SO4. The organic layers were concentrated and purified by column chromatography on silica gel to give (1S,3S)-3-(benzo[d]thiazol-2-ylamino)cyclobutanol (160 mg, 0.72 mmol, yield 73%). ESI-MS (M+1): 221 calc. for C11H12N2OS 221.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08952037B2 |
|---|
| Source dataset | uspto-grants-2015_02 |
|---|
| ORD ID | ord-49f1ae679ebb4e15927cf50b35cd9fb4 |
|---|
| Source note | uspto-grants-2015_02 |
|---|