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

HRID 471264

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].[C:12]1([C:18]2[S:19][CH:20]=[C:21]([C:23]([N:25]3[CH2:30][C:29]4([CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)[O:28][CH2:27][CH2:26]3)=[O:24])[N:22]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.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:33]1[CH2:34][CH2:35][C:29]2([O:28][CH2:27][CH2:26][N:25]([C:23]([C:21]3[N:22]=[C:18]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[S:19][CH:20]=3)=[O:24])[CH2:30]2)[CH2:31][CH2:32]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 9-bromo-1-nonanol (0.346 g) in MeCN (3 mL) was added to solution of (2-phenylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone (example 112, step b) (0.355 g) and triethylamine (0.288 mL) in MeCN (7 mL). The resulting mixture was stirred at 60° C. under argon for 17 h. After cooling to RT the solvent was removed in vacuo. The residue was taken up in DCM, washed with brine (×2), dried over sodium sulphate, filtered and evaporated in vacuo. The yellow oil was purified by silica gel chromatography eluting with 0-7% MeOH in DCM to give the subtitled compound as a white solid. Yield 0.378 g.

Workup

temperatureAfter cooling to RT the solvent
customwas removed in vacuo
washwashed with brine (×2)
dry with materialdried over sodium sulphate
filtrationfiltered
customevaporated in vacuo
customThe yellow oil was purified by silica gel chromatography
washeluting with 0-7% MeOH in DCM

Sources & evidence

ORD record: ord-9bf6d33fe5944fb0b3e56c78ee538948
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629271B2

Linked notes

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