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-chloro-4-ethoxyphenyl)-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl)methyl)propane-1,3-diol
Reaction equation
C(OC(=O)[NH:7][C:8]1([CH2:16][N:17]2[C:25]3[C:20](=[C:21]([C:26]4[N:30]=[C:29]([C:31]5[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH3:39])=[C:33]([Cl:40])[CH:32]=5)[O:28][N:27]=4)[CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)[CH2:13][O:12]C(C)(C)[O:10][CH2:9]1)(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>>[NH2:7][C:8]([CH2:16][N:17]1[C:25]2[C:20](=[C:21]([C:26]3[N:30]=[C:29]([C:31]4[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH3:39])=[C:33]([Cl:40])[CH:32]=4)[O:28][N:27]=3)[CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18]1)([CH2:9][OH:10])[CH2:13][OH:12]Participants
3
Reactant 2
Product 1
Procedure
When the product of Step D 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 83.3% yield, as off white solid. 1H-NMR (DMSO-d6) 1.46 (tr, 3H, J=6.85 Hz); 2.99-3.44 (m, 4H); 3.52 (tr, 2H, J=8.96 Hz); 3.71 (tr, 4H, J=10.46 Hz); 4.15 (q, 2H, J=6.97, 13.97 Hz); 6.77 (d, 1H, J=8.12 Hz); 6.99 (d, 1H, J=8.65 Hz); 7.17 (tr, 2H, J=7.74 Hz); 7.45 (d, 1H, J=8.68 Hz); 7.98 (d, 1H, J=8.75 Hz); 8.14, (broad s, 1H).
Sources & evidence
- ORD record
- ord-4d7f0615037942e1a2acfccf949bf91c
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181182B2
Reaction notes
Loading…