tert-Butyl-5-((4-(3-(6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-yl)prop-1-ynyl)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate → tert-Butyl-5-(4-(N-(3-methoxyphenyl)-N-methylsulfamoyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate
Reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([S:24](=[O:36])(=[O:35])[N:25]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=3)[CH3:26])=[CH:20][CH:19]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(OC(=O)NC1(C#CC2C=CC(C#CCN3C4C(=CC=C(OC)C=4)C(C(=O)C4C=C(OC)C(OC)=C(OC)C=4)=C3)=CC=2)COC(C)(C)OC1)(C)(C)C>>[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([S:24](=[O:35])(=[O:36])[N:25]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=3)[CH3:26])=[CH:22][CH:23]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:2])([CH3:3])[CH3:4]Participants
3
Reactant 2
Product 1
Procedure
When the product of Step C was substituted for tert-butyl-5-((4-(3-(6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-yl)prop-1-ynyl)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate in Example 14, Step D, the similar process afforded the title compound in 59%, as creamy paste. 1H-NMR (CDCl3) 1.45 (s, 3H); 1.46 (s, 9H); 1.49 (s, 3H); 1.58 (s, 2H); 2.63 (5, 2H); 3.13 (s, 3H); 3.75 (s, 3H), 3.96 (d, 2H, J=17.23 Hz); 4.07 (d, 2H, J=17.23 Hz); 6.54 (dd, 1H, J=1.66, 7.92 Hz); 6.69 (tr, 1H, J=2.18 Hz); 6.79 (dd, 1H, J=2.39, 10.68 Hz); 7.16 (tr, 1H, J=8.15 Hz); 7.47 (s, 4H).
Sources & evidence
- ORD record
- ord-f7a93664aa114d8c8a91359310941557
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181182B2
Reaction notes
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