Triethylamine → (9-(3-(Diethoxymethyl)phenethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone

HRID 471012Notes

Reaction equation

CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])[CH:9]=1)(=O)=O.FC(F)(F)C(O)=O.[CH3:28][C:29]1[S:33][C:32]([C:34]([N:36]2[CH2:41][C:40]3([CH2:46][CH2:45][NH:44][CH2:43][CH2:42]3)[O:39][CH2:38][CH2:37]2)=[O:35])=[CH:31][CH:30]=1.C(N(CC)CC)C>C(#N)C>[CH2:19]([O:18][CH:14]([O:15][CH2:16][CH3:17])[C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH2:7][CH2:6][N:44]1[CH2:45][CH2:46][C:40]2([O:39][CH2:38][CH2:37][N:36]([C:34]([C:32]3[S:33][C:29]([CH3:28])=[CH:30][CH:31]=3)=[O:35])[CH2:41]2)[CH2:42][CH2:43]1)[CH3:20]

Participants

Conditions

Temperature: 70 °C

Procedure

3-(Diethoxymethyl)phenethyl methanesulfonate (example 20, step d) (0.30 g) in acetonitrile (1.5 mL) was added to a stirred solution of (5-methylthiophen-2-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate (example 9, step b) (0.391 g) and triethylamine (0.415 mL) in acetonitrile (1.5 mL) and the solution heated at 70° C. for 48 h. After cooling, the solution was evaporated in vacuo and applied to a silica gel column for purification, eluting with ethyl acetate:isohexane:triethylamine, 60:40:5 giving the subtitled compound as a gum. Yield 0.2 g.

Workup

temperatureAfter cooling
customthe solution was evaporated in vacuo
customapplied to a silica gel column for purification
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-a50832302a314e68870b6ab32fa48645
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629271B2

Reaction notes

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