1-Hydroxybenzotriazole → Methyl 2-(2-(4'-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetamido)acetate

A solution of 2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetic acid (Example 1; 250 mg, 0.63 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (151 mg, 0.79 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (85 mg, 0.63 mmol) and N-ethyl-N-isopropylpropan-2-amine (242 μL, 1.39 mmol) in DMF (2499 μL) was treated with a solution of methyl 2-aminoacetate hydrochloride (87 mg, 0.69 mmol) in DMF (417 μL) at 23° C. The resulting solution was stirred at RT for 4 hours. The reaction mixture was evaporated to dryness and redissolved in EtOAc (25 mL), and washed sequentially with saturated brine (50 mL) and water (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford methyl 2-(2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetamido)acetate (266 mg, 90%) which was used without further purification.

1. customThe reaction mixture was evaporated to dryness
2. dissolutionredissolved in EtOAc (25 mL)
3. washwashed sequentially with saturated brine (50 mL) and water (50 mL)
4. dry with materialThe organic layer was dried over MgSO4
5. filtrationfiltered
6. customevaporated

ORD-Eintrag

ord-33db9c1a1e1546fe9514de9c099af28a

Quelldatensatz

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08188092B2