Triethylamine → (2-Cyclopropylthiazol-4-yl)(9-(3-fluoro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.34 g) was added to a solution of 2-(3-(1-oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)-5-fluorophenyl)ethanol (example 55, step c) (0.21 g), 2-cyclpropylthiazole-4-carboxylic acid (example 57, step c) (0.12 g) and triethylamine (0.38 mL) in DMF (7 mL) and the resulting yellow solution was stirred for 30 min. The mixture was partitioned between ethyl acetate and brine (100 mL), the organic layer was washed with brine (2×100 mL), dried over sodium sulphate, filtered and the solvent evaporated. The resulting gum was purified by silica gel chromatography eluting with 47.5:47.5:5 isohexane:ethyl acetate:triethylamine to 95:5 ethyl acetate:triethylamine gradient. The fractions containing product were combined, toluene (200 mL) was added and the solvent evaporated under reduced pressure to give the subtitled compound as a clear gum. Yield 0.15 g.

1. customThe mixture was partitioned between ethyl acetate and brine (100 mL)
2. washthe organic layer was washed with brine (2×100 mL)
3. dry with materialdried over sodium sulphate
4. filtrationfiltered
5. customthe solvent evaporated
6. customThe resulting gum was purified by silica gel chromatography
7. washeluting with 47.5:47.5:5 isohexane
8. additionThe fractions containing product
9. additiontoluene (200 mL) was added
10. customthe solvent evaporated under reduced pressure

ORD record

ord-daf805d1a4304854ae2e22c737715878

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629271B2