Water → HCID 57504475, compound

A stirred solution of 2-bromo-4-(2-methoxyethoxy)butanoic acid (Step 4) (200 mg, 0.83 mmol) in thionyl chloride (4 mL) was refluxed for 30 minutes. The reaction mixture was concentrated in vacuo to remove excess thionyl chloride. The residue was dissolved in DCM (2 mL) and was added slowly to a stirred solution of 2-amino-4-methylthiazole (99.5 mg, 0.871 mmol) and DIPEA (117.9 mg, 0.913 mmol) in DCM (4 mL). The reaction mixture was kept at ambient temperature for 1 h before water was added and the two phases were separated. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with EtOAc/MeOH:1/1) to give the title compound as an oil (105 mg), 1H NMR (300 MHz, CDCl3) δ 6.57 (d, 1H), 4.72 (dd, 1H), 3.66 (m, 2H), 3.60 (m, 2H), 3.51 (m, 2H), 3.36 (s, 3H), 2.50 (m, 1H), 2.31 (m, 4H).

1. concentrationThe reaction mixture was concentrated in vacuo
2. customto remove excess thionyl chloride
3. dissolutionThe residue was dissolved in DCM (2 mL)
4. additionwas added
5. customthe two phases were separated
6. dry with materialThe organic phase was dried over MgSO4
7. concentrationconcentrated in vacuo
8. customThe residue was purified with column chromatography (silica gel, eluting with EtOAc/MeOH:1/1)

ORD record

ord-df7dc99dbaa74e57b2c3c73fbdd42e04

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143263B2