Triethylamine → 4-(3-(4-(2-Methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)propoxy)benzaldehyde

HRID 470976Notes

Reaction equation

FC(F)(F)C(O)=O.[CH3:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([N:16]2[CH2:21][C:20]3([CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[O:19][CH2:18][CH2:17]2)=[O:15])[N:13]=1.Br[CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=[O:37])=[CH:34][CH:33]=1.C(N(CC)CC)C>CC#N>[CH3:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([N:16]2[CH2:21][C:20]3([CH2:26][CH2:25][N:24]([CH2:28][CH2:29][CH2:30][O:31][C:32]4[CH:39]=[CH:38][C:35]([CH:36]=[O:37])=[CH:34][CH:33]=4)[CH2:23][CH2:22]3)[O:19][CH2:18][CH2:17]2)=[O:15])[N:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of (2-methylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate (example 4, step h) (0.244 g), 4-(3-bromopropoxy)benzaldehyde (example 8, step a) (0.15 g) and triethylamine (0.344 mL) in MeCN (2 mL) was heated at 60° C. After 16 h, the reaction mixture was evaporated in vacuo. Purification was by silica gel chromatography eluting with ethyl acetate:triethylamine, 10:1 to give the subtitled compound as an oil. Yield 0.24 g.

Workup

customthe reaction mixture was evaporated in vacuo
customPurification
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-6fb56f44e79644ab861bddd6415b5ac9
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629271B2

Reaction notes

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