Methyl iodide → 4-(2-Ethoxy-2-oxoethyl)-1,1-dimethyl-4-(5-(phenylethynyl)furan-2-carboxamido)-piperidinium iodide
Reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])([NH:8][C:9]([C:11]2[O:12][C:13]([C:16]#[C:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:15]=2)=[O:10])[CH2:4][CH2:3]1.[CH3:30][I:31]>>[I-:31].[CH2:28]([O:27][C:25](=[O:26])[CH2:24][C:5]1([NH:8][C:9]([C:11]2[O:12][C:13]([C:16]#[C:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:15]=2)=[O:10])[CH2:4][CH2:3][N+:2]([CH3:30])([CH3:1])[CH2:7][CH2:6]1)[CH3:29]Participants
3
Procedure
Ethyl 2-(1-methyl-4-(5-(phenylethynyl)furan-2-carboxamido)piperidin-4-yl)acetate (51 mg, 0.129 mmol) was treated with MeI (80 uL, 1.29 mmol) as described in Example 2a to yield crude title compound (68 mg, 97%) which was used without further purification. 1H NMR (400 MHz, CD3OD) δ 7.57-7.53 (m, 2H), 7.47-7.42 (m, 3H), 7.21 (s, 1H), 6.87 (s, 1H), 4.11 (q, 2H, J=7.2 Hz), 3.58-3.42 (m, 4H), 3.22 (s, 3H), 3.21 (s, 3H), 3.02 (s, 2H), 2.90-2.83 (m, 2H), 2.29-2.19 (m, 2H), 1.18 (t, 3H, J=7.2 Hz); MS ESI 409.3 [M+H]+, calcd for [C24H28N2O4+H]+ 409.50.
Sources & evidence
- ORD record
- ord-4837ea3ac1fb469b9baa5a5774c3991d
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680282B2
Reaction notes
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