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-(3,4-di-propoxyphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)propane-1,3-diol
Reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH2:22][CH2:23][N:24]4[CH2:29][C:30]3([NH:38]C(=O)OC(C)(C)C)[CH2:35][O:34]C(C)(C)[O:32][CH2:31]3)[N:16]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][CH3:14])[CH2:2][CH3:3].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>>[NH2:38][C:30]([CH2:29][N:24]1[C:25]2[C:21](=[C:20]([C:17]3[N:16]=[C:15]([C:7]4[CH:8]=[CH:9][C:10]([O:11][CH2:12][CH2:13][CH3:14])=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[CH:6]=4)[O:19][N:18]=3)[CH:28]=[CH:27][CH:26]=2)[CH2:22][CH2:23]1)([CH2:31][OH:32])[CH2:35][OH:34]Participants
3
Reactant 2
Product 1
Procedure
When the product of Step E 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 67% yield., as a colourless solid. 1H-NMR (DMSO-d6) 0.95-1.01 (m, 6H); 1.37 (s, 2H); 1.68-1.8 (m, 4H); 2.98 (s, 2H); 3.2-3.3 (m, 6H+H2O); 3.5-3.57 (m, 2H); 3.9-4.05 (m, 4H); 4.55 (broad s, 2H); 6.77 (d, 1H, J=9 Hz); 7.1-7.26 (m, 3H); 7.58 (d, 1H, J=3 Hz); 7.71 (dd, 1H, J=3, 9 Hz).
Sources & evidence
- ORD record
- ord-314909acd44f4831a7aaf6445ed2a6a4
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181182B2
Reaction notes
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