Triethylamine → HCID 57989137, compound

HRID 1689488Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].FC(F)(F)C(O)=O.[CH:19]([C:22]1[S:23][CH:24]=[C:25]([C:27]([N:29]2[CH2:34][C:33]3([CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[O:32][CH2:31][CH2:30]2)=[O:28])[N:26]=1)([CH3:21])[CH3:20].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:37]1[CH2:38][CH2:39][C:33]2([O:32][CH2:31][CH2:30][N:29]([C:27]([C:25]3[N:26]=[C:22]([CH:19]([CH3:20])[CH3:21])[S:23][CH:24]=3)=[O:28])[CH2:34]2)[CH2:35][CH2:36]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 9-bromo-1-nonanol (0.316 g) in MeCN (3 mL) was added to solution of (2-isopropylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate (example 22, step b) (0.40 g) and triethylamine (0.395 mL) in MeCN (7 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, washed with brine (×2), dried over sodium sulphate, filtered and evaporated in vacuo. The orange solid was purified by silica gel chromatography eluting with 0-10% MeOH in DCM to give the subtitled compound as an off-white solid. Yield 0.325 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 orange solid was purified by silica gel chromatography
washeluting with 0-10% MeOH in DCM

Sources & evidence

ORD record: ord-c143d005a5ed4d46b037c6d673c706a2
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148373B2

Reaction notes

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