Tert-butyl 5-(5-(5-(3-chloro-4-propoxy phenyl)-1,2,4-oxadiazol-3-yl)benzofuran-2-yl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate → HCID 46200295, compound

HRID 2046120Notes

Reaction equation

HRID 2046120 reaction equation
ClC1C=C(C2ON=C(C3C=CC4OC(C5(NC(=O)OC(C)(C)C)COC(C)(C)OC5)=CC=4C=3)N=2)C=CC=1OCCC.[Cl:42][C:43]1[C:67]([C:68]2[N:72]=[C:71]([C:73]3[CH:78]=[CH:77][C:76]([CH2:79][CH2:80][CH3:81])=[CH:75][CH:74]=3)[O:70][N:69]=2)=[CH:66][C:46]2[CH:47]=[C:48]([C:50]3([NH:58]C(=O)OC(C)(C)C)[CH2:55][O:54]C(C)(C)[O:52][CH2:51]3)[O:49][C:45]=2[CH:44]=1>>[NH2:58][C:50]([C:48]1[O:49][C:45]2[CH:44]=[C:43]([Cl:42])[C:67]([C:68]3[N:72]=[C:71]([C:73]4[CH:74]=[CH:75][C:76]([CH2:79][CH2:80][CH3:81])=[CH:77][CH:78]=4)[O:70][N:69]=3)=[CH:66][C:46]=2[CH:47]=1)([CH2:51][OH:52])[CH2:55][OH:54]

Participants

3

Reactant 2

HCID 66614932Tert-butyl 5-(5-(5-(3-chloro-4-propoxy phenyl)-1,2,4-oxadiazol-3-yl)benzofuran-2-yl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamateHCID 68002033HCID 68002033, compound

Product 1

HCID 46200295HCID 46200295, compoundYield 40%

Procedure

When tert-butyl 5-(5-(5-(3-chloro-4-propoxyphenyl)-1,2,4-oxadiazol-3-yl)benzofuran-2-yl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate was replaced with the tert-butyl 5-(6-chloro-5-(5-(4-propylphenyl)-1,2,4-oxadiazol-3-yl)benzofuran-2-yl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate (obtained as crude via a process as described in Example 36, Step D) the similar procedure as in Example 36, Step E gave the title compound (0.006 g, 40%) as white solid. 1H NMR (CD3OD) 8.12 (d, 2H, J=8.28 Hz); 8.12 (s, 1H); 7.75 (s, 1H); 7.43 (d, 2H, J=8.31 Hz); 6.9 (s, 1H); 3.88 (d, 2H, J=10.9 Hz); 3.78 (d, 1H, J=10.9 Hz); 2.7 (t, 2H, J=7.41 Hz); 1.76-1.64 (m, 2H); 0.97 (t, 3H, J=7.32 Hz).

Workup

  1. customobtained as crude via a process

Sources & evidence

ORD record
ord-eeb73e7b7c564df296f307e615e6b145
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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