Triethylamine → Benzo[d]thiazol-2-yl(9-(9-hydroxynonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

HRID 1689483Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 9-bromo-1-nonanol (0.335 g) in acetonitrile (3 mL) was added to a solution of benzo[d]thiazol-2-yl(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone (example 106, step b) (0.34 g) and triethylamine (0.278 mL) in acetonitrile (7 mL). The resulting mixture was stirred at 60° C. overnight. The reaction mixture was evaporated in vacuo and the residue was taken up into DCM (30 mL), washed with brine (2×15 mL), dried over sodium sulphate, filtered and evaporated in vacuo. Purification was by silica gel chromatography eluting with 0-10% methanol in dichloromethane to give the subtitled compound as a white solid. Yield 0.34 g.

Workup

customThe reaction mixture was evaporated in vacuo
washwashed with brine (2×15 mL)
dry with materialdried over sodium sulphate
filtrationfiltered
customevaporated in vacuo
customPurification
washeluting with 0-10% methanol in dichloromethane

Sources & evidence

ORD record: ord-d40f10a8e6ef4f398198ff956dd90608
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148373B2

Reaction notes

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