Triethylamine → (9-(9-Hydroxynonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-5-yl)methanone

HRID 471268Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].[CH:12]([C:15]1[S:16][C:17]([C:20]([N:22]2[CH2:27][C:26]3([CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[O:25][CH2:24][CH2:23]2)=[O:21])=[CH:18][N:19]=1)([CH3:14])[CH3:13].C(N(CC)CC)C>CC#N>[OH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:30]1[CH2:31][CH2:32][C:26]2([O:25][CH2:24][CH2:23][N:22]([C:20]([C:17]3[S:16][C:15]([CH:12]([CH3:13])[CH3:14])=[N:19][CH:18]=3)=[O:21])[CH2:27]2)[CH2:28][CH2:29]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 9-bromo-1-nonanol (0.446 g) in MeCN (3.9 mL) was added to solution of (2-isopropylthiazol-5-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone (example 114, step b) (0.395 g) and triethylamine (0.36 mL) in MeCN (8.6 mL). The resulting mixture was stirred at 60° C. under argon for 16 h. After cooling to RT the solvent was removed in vacuo. The residue was taken up in DCM (25 mL), washed with brine (20 mL) and water (20 mL), dried over sodium sulphate, filtered and evaporated in vacuo. The residue was purified by silica gel chromatography eluting with 0-10% MeOH in DCM to give the subtitled compound as a white solid. Yield 0.329 g.

Workup

temperatureAfter cooling to RT the solvent
customwas removed in vacuo
washwashed with brine (20 mL) and water (20 mL)
dry with materialdried over sodium sulphate
filtrationfiltered
customevaporated in vacuo
customThe residue was purified by silica gel chromatography
washeluting with 0-10% MeOH in DCM

Sources & evidence

ORD record: ord-48628d012589419c93252521c526da82
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629271B2

Reaction notes

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