HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → HCID 67442421, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | (2S)-4-amino-2-(((tert-butoxy)carbonyl)amino)butanoic acid | HCID 7019666 | — |
| Reactant | 1-Cyclopropyl-3-(3-fluoro-4-(2-(5-formylpyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)urea | HCID 58236579 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67442421 | HCID 67442421 | 37.3% |
Reaction Steps
To a suspension of 47 (230 mg, 0.51 mmol, scheme 15) in DCM (5.1 mL) were added (S)-4-amino-2-(tert-butoxycarbonylamino)butanoic acid (224 mg, 1.03 mmol) and acetic acid (59 μl, 1.03 mmol). After stirring for 20 min at room temperature, NaBH(OAc)3 (326 mg, 1.54 mmol) was added. The reaction mixture was stirred for 16 h, quenched by addition of 1N NaOH, and concentrated. The solid was collected by filtration and purified by Biotage (SNAP 50 g cartridge; MeOH/DCM: 0/100 to 20/80 over 20 CV), to afford the title compound 107 (120 mg, 0.19 mmol, 37% yield). MS (m/z): 633.7 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08906852B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-f211849dbb4f426296695a1ed3423f5d |
| Source note | uspto-grants-2014_12 |