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 46200150, compound

HRID 2046126Notes

Reaction equation

CC1(C)[O:7][CH2:6][C:5]([NH:35]C(=O)OC(C)(C)C)([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17]4[N:21]=[C:20]([C:22]5[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH3:31])=[C:24]([N+:32]([O-:34])=[O:33])[CH:23]=5)[O:19][N:18]=4)=[CH:13][C:11]=3[CH:12]=2)[CH2:4][O:3]1.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>>[NH2:35][C:5]([C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]3[N:21]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH3:31])=[C:24]([N+:32]([O-:34])=[O:33])[CH:23]=4)[O:19][N:18]=3)=[CH:13][C:11]=2[CH:12]=1)([CH2:4][OH:3])[CH2:6][OH:7]

Participants

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-ylcarbamate

HCID 86660632tert-Butyl 2,2-dimethyl-5-(5-(5-(3-nitro-4-propoxyphenyl)-1,2,4-oxadiazol-3-yl)benzofuran-2-yl)-1,3-dioxan-5-ylcarbamate

Product 1

HCID 46200150HCID 46200150, compoundYield 49%

Procedure

When the product of Step D was substituted for 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 in Example 36, Step E, the similar procedure afforded the title compound in 49% yield, as creamy solid. 1H NMR (DMSO-d6) 8.6 (s, 1H); 8.37 (d, 1H, J=8.37 Hz); 8.31 (s, 1H); 7.94 (d, 1H, J=8.52 Hz); 7.68 (d, 1H, J=8.52 Hz); 7.59 (d, 1H, J=8.82 Hz); 6.91 (s, 1H); 4.87 (b, 2H); 4.23 (t, 2H, J=5.82 Hz); 3.67 (d, 2H, J=10.05 Hz); 3.58 (d, 2H, J=9.96 Hz); 1.78-1.71 (m, 2H); 0.97 (t, 3H, J=7.26 Hz).

Sources & evidence

ORD record: ord-effc5d0080574a33bf12eedea41f578a
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592399B2

Reaction notes

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