Tert-butyl 5-((4-(3-(4-fluorophenylamino)prop-1-ynyl)phenyl)-ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate → tert-Butyl-5-(4-(3-(4-fluorophenylamino)propyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]3([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22][CH2:21]3)=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(OC(=O)NC1(C#CC2C=CC(S(=O)(=O)NC3CCC4CC3C4(C)C)=CC=2)COC(C)(C)OC1)(C)(C)C>>[C:31]([O:30][C:29](=[O:35])[NH:28][C:20]1([CH2:19][CH2:18][C:15]2[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][CH2:9][NH:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[CH:13][CH:14]=2)[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22][CH2:21]1)([CH3:32])([CH3:33])[CH3:34]Participants
3
Reactant 2
Product 1
Procedure
When the product of Step B was substituted for tert-butyl-5-((4-(N-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)sulfamoyl)phenyl-)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate in Example 19, Step C, the similar process afforded the title compound in 94% yield, as creamy gum. 1H-NMR (CDCl3) 1.42 (s, 3H); 1.44 (s, 3H); 1.46 (s, 9H); 1.87-1.96 (m, 4H); 2.5-2.56 (m, 2H); 2.67 (tr, 2H, J=7.32 Hz); 3.04 (tr, 2H, J=7.05 Hz); 3.86 (d, 2H, J=11.8 Hz); 3.88 (d, 2H, J=11.7 Hz); 4.9 (s, 1H); 6.45-6.50 (m, 2H); 6.82-6.88 (m, 2H); 7.09 (s, 4H).
Sources & evidence
- ORD record
- ord-20ac875a84ab412e8ea9f9d908c56dd9
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181182B2
Reaction notes
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