Tert-butyl 5-(5-(5-(3-chloro-4-propoxy phenyl)-1,2,4-oxadiazol-3-yl)benzofuran-2-yl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate → 2-Amino-2-(5-(5-(4-Propoxy-3-methoxyphenyl)-1,2,4-oxadiazol-3-yl)benzofuran-2-yl)propane-1,3-diol
Reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:17]=[CH:18][C:19]4[O:23][C:22]([C:24]5([NH:32]C(=O)OC(C)(C)C)[CH2:29][O:28]C(C)(C)[O:26][CH2:25]5)=[CH:21][C:20]=4[CH:40]=3)[N:12]=2)=[CH:7][C:6]=1[O:41][CH3:42])[CH2:2][CH3:3].ClC1C=C(C2ON=C(C3C=CC4OC(C5(NC(=O)OC(C)(C)C)COC(C)(C)OC5)=CC=4C=3)N=2)C=CC=1OCCC>>[NH2:32][C:24]([C:22]1[O:23][C:19]2[CH:18]=[CH:17][C:16]([C:13]3[N:12]=[C:11]([C:8]4[CH:9]=[CH:10][C:5]([O:4][CH2:1][CH2:2][CH3:3])=[C:6]([O:41][CH3:42])[CH:7]=4)[O:15][N:14]=3)=[CH:40][C:20]=2[CH:21]=1)([CH2:25][OH:26])[CH2:29][OH:28]Participants
3
Reactant 2
Product 1
Procedure
When the product of Step C was substituted for tert-butyl 5-(5-(5-(3-chloro-4-propoxyphenyl)-1,2,4-oxadiazol-3-yl)benzofuran-2-yl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate in Example 36, Step E, the similar procedure afforded the title compound in 57% yield, as colourless solid. 1H-NMR (DMSO-d6) 8.28 (s, 1H); 7.92 (d, 1H, J=2.82 Hz); 7.61 (m, 3H); 7.16 (d, 1H, J=8.53 Hz); 6.88 (s, 1H); 4.78 (b, 2H); 4.01 (t, 2H, J=6.03 Hz); 3.99 (s, 3H); 3.77-3.57 (m, 4H); 1.78-1.71 (m, 2H); 0.96 (t, 3H, J=7.29 Hz).
Sources & evidence
- ORD record
- ord-ebd4b16d663842d490e0970742a8dba8
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193716B2
Reaction notes
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