Triethylamine → (9-(3-(2-Hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(4-isopropylthiazol-2-yl)methanone

HRID 1689369Notes

Reaction equation

[CH:1]([C:4]1[N:5]=[C:6]([C:9]([N:11]2[CH2:16][C:15]3([CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[O:14][CH2:13][CH2:12]2)=[O:10])[S:7][CH:8]=1)([CH3:3])[CH3:2].Br[CH2:23][C:24]1[CH:25]=[C:26]([CH2:30][CH2:31][OH:32])[CH:27]=[CH:28][CH:29]=1.C(N(CC)CC)C>C(#N)C>[OH:32][CH2:31][CH2:30][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[CH2:23][N:19]1[CH2:18][CH2:17][C:15]2([O:14][CH2:13][CH2:12][N:11]([C:9]([C:6]3[S:7][CH:8]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=3)=[O:10])[CH2:16]2)[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of (4-isopropylthiazol-2-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone (example 66, step b) (0.28 g) and 2-(3-(bromomethyl)phenyl)ethanol (example 6, step a) (0.171 g) in acetonitrile (20 mL) was treated with triethylamine (0.276 mL) and the reaction mixture stirred for 2 hours at 20° C. The solvent was evaporated under reduced pressure and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was dried over sodium sulphate, filtered and the solvent removed under reduced pressure. The crude product was purified by flash silica chromatography using 2.5% methanol in dichloromethane with 1% triethylamine as solvent to afford the subtitled compound. Yield 0.25 g.

Workup

customThe solvent was evaporated under reduced pressure
customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
dry with materialThe organic layer was dried over sodium sulphate
filtrationfiltered
customthe solvent removed under reduced pressure
customThe crude product was purified by flash silica chromatography

Sources & evidence

ORD record: ord-9bae18689c064648af7e26097cfd64a8
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148373B2

Reaction notes

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