Ethane, 2-bromo-1,1-diethoxy- → HCID 59837507, compound

HRID 272972Notes

Reaction equation

HRID 272972 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4([C:24](=[S:26])[NH2:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:14][CH:13]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[CH2:27](OC(OCC)CBr)[CH3:28]>>[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4([C:24]5[S:26][CH:27]=[CH:28][N:25]=5)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:14][CH:13]=3)[CH2:7][CH2:6]2)[CH2:2][CH2:3][CH2:4]1

Participants

3

Reactant 2

HCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 86601904HCID 86601904, compound

Product 1

HCID 59837507HCID 59837507, compoundYield 39%

Procedure

The title compound (92 mg, 39%) was prepared from 4-{4-[(1-cyclobutylpiperidin-4-yl)oxy]phenyl}tetrahydro-2H-pyran-4-carbothioamide and bromoacetaldehyde diethylacetal similarly to the procedure used for example 137. 1H NMR (400 MHz, CDCl3) δ 1.66-1.72 (m, 2H), 1.77-1.89 (m, 5H), 1.95-2.04 (m, 4H), 2.11 (m, 1H), 2.36-2.43 (m, 2H), 2.58-2.72 (m, 5H), 3.71 (t, 2H), 3.84-3.88 (m, 2H), 4.27 (m, 1H), 6.84 (d, 2H), 7.23-7.26 (m, 3H), 7.70 (s, 1H). LRMS APCI+ m/z 399 [MH]+.

Sources & evidence

ORD record
ord-32731cc8177944d1ac11b61ad96bf671
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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