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 → 2-Amino-2-[5-[5-(3-chloro-4-thiophen-3-ylphenyl)-1,2,4-oxadiazol-3-yl]-1-benzofuran-2-yl]propane-1,3-diol

HRID 2046103Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][C:21]4[O:25][C:24]([C:26]5([NH:34]C(=O)OC(C)(C)C)[CH2:31][O:30]C(C)(C)[O:28][CH2:27]5)=[CH:23][C:22]=4[CH:42]=3)[N:14]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[CH:12]=[CH:11][S:10][CH:9]=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>>[NH2:34][C:26]([C:24]1[O:25][C:21]2[CH:20]=[CH:19][C:18]([C:15]3[N:14]=[C:13]([C:4]4[CH:5]=[CH:6][C:7]([C:8]5[CH:12]=[CH:11][S:10][CH:9]=5)=[C:2]([Cl:1])[CH:3]=4)[O:17][N:16]=3)=[CH:42][C:22]=2[CH:23]=1)([CH2:27][OH:28])[CH2:31][OH:30]

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 86660624tert-Butyl 5-(5-(5-(3-chloro-4-(thiophen-3-yl)phenyl)-1,2,4-oxadiazol-3-yl)benzofuran-2-yl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Product 1

HCID 461999902-Amino-2-[5-[5-(3-chloro-4-thiophen-3-ylphenyl)-1,2,4-oxadiazol-3-yl]-1-benzofuran-2-yl]propane-1,3-diolYield 48%

Procedure

When the product of Step A was substituted for 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 in Example 36, Step E, the similar procedure afforded the title compound in 48% yield, as colourless solid. 1H-NMR (DMSO-d6) 8.42 (s, 1H); 8.28 (s, 1H); 8.2 (d, 1H, J=8.41 Hz); 8.11 (d, 1H, J=8.1 Hz); 7.82 (s, 1H); 7.64-7.61 (m, 3H); 7.4 (b, 1H); 6.92 (s, 1H); 4.9 (bs, 2H); 3.66 (b, 2H); 3.59 (b, 2H).

Sources & evidence

ORD record: ord-ddd1fb960ea24c77a8ce09d281ca1272
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592399B2

Reaction notes

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