tert-Butyl 5-((4-(5-(3,4-diethoxyphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate → 2-Amino-2-((4-(5-(3-amino-4-propoxyphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)propane-1,3-diol
Reaction equation
C(OC([NH:8][C:9]1[CH:10]=[C:11]([C:19]2[O:23][N:22]=[C:21]([C:24]3[CH:32]=[CH:31][CH:30]=[C:29]4[C:25]=3[CH2:26][CH2:27][N:28]4[CH2:33][C:34]3([NH:42]C(=O)OC(C)(C)C)[CH2:39][O:38]C(C)(C)[O:36][CH2:35]3)[N:20]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH2:17][CH3:18])=O)(C)(C)C.C(OC1C=C(C2ON=C(C3C=CC=C4C=3CCN4CC3(NC(=O)OC(C)(C)C)COC(C)(C)OC3)N=2)C=CC=1OCC)C>>[NH2:42][C:34]([CH2:33][N:28]1[C:29]2[C:25](=[C:24]([C:21]3[N:20]=[C:19]([C:11]4[CH:12]=[CH:13][C:14]([O:15][CH2:16][CH2:17][CH3:18])=[C:9]([NH2:8])[CH:10]=4)[O:23][N:22]=3)[CH:32]=[CH:31][CH:30]=2)[CH2:26][CH2:27]1)([CH2:35][OH:36])[CH2:39][OH:38]Participants
3
Reactant 2
Product 1
Procedure
When the product of Step F was substituted for tert-butyl 5-((4-(5-(3,4-diethoxyphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate in Example 34, Step E, the identical process afforded the title compound in 70% yield, as a creamy solid. 1H-NMR (DMSO-d6) 0.92-1.05 (m, 3H); 1.42 (broad s, 2H); 1.7-1.81 (m, 2H); 2.99 (s, 2H); 2.42-2.51 (m, 2H); 2.95 (s, 2H); 3.11-3.4 (m, 2H, +H2O); 3.53 (tr, 2H, J=9 Hz); 3.93-4.05 (m, 2H); 4.56 (m, 2H); 5.11 (s, 2H); 6.76 (d, 1H, J=6 Hz); 6.97 (d, 1H, J=9 Hz); 7.0 (d, 1H, J=6 Hz); 7.1-7.25 (m, 2H); 7.32-7.42 (m, 2H).
Sources & evidence
- ORD record
- ord-afba2de9fe2a49ff85125c6408288ab8
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181182B2
Reaction notes
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