tert-Butyl 5-((4-(5-(4-propylphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate → HCID 46195603, compound

HRID 710411Notes

Reaction equation

[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:23]=[CH:22][CH:21]=[C:20]4[C:16]=3[CH2:17][CH2:18][N:19]4[CH2:24][C:25]3([NH:33]C(=O)OC(C)(C)C)[CH2:30][O:29]C(C)(C)[O:27][CH2:26]3)[N:11]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3].C(OC1C=C(C2ON=C(C3C=CC=C4C=3CCN4CC3(NC(=O)OCCCC)COC(C)(C)OC3)N=2)C=CC=1OCC)C>>[NH2:33][C:25]([CH2:24][N:19]1[C:20]2[C:16](=[C:15]([C:12]3[N:11]=[C:10]([C:7]4[CH:6]=[CH:5][C:4]([CH2:1][CH2:2][CH3:3])=[CH:9][CH:8]=4)[O:14][N:13]=3)[CH:23]=[CH:22][CH:21]=2)[CH2:17][CH2:18]1)([CH2:30][OH:29])[CH2:26][OH:27]

Participants

Reactant 2

HCID 86661797tert-Butyl 5-((4-(5-(4-propylphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HCID 86661798HCID 86661798, compound

Product 1

HCID 46195603HCID 46195603, compoundYield 80%

Procedure

When the product of Step C was substituted for tea-butyl 5-((4-(5-(3,4-diethoxyphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate in Example 34, Step E, the identical process afforded the title compound in 80% yield, as a creamy solid. 1H-NMR (DMSO-d6) 0.85-0.95 (m, 3H); 1.33 (broad s, 2H); 2.6-2.66 (m, 2H); 2.98 (s, 2H); 3.2-3.34 (m, 8H+H2O); 3.54 (tr, 2H, J=8.3 Hz); 4.56 (broad s, 2H); 6.77 (d, 1H, J=7.77 Hz); 7.1-7.26 (m, 2H); 7.38-7.49 (m, 2H); 7.9-8.1 (m, 2H).

Sources & evidence

ORD record: ord-32cc86c197bd45398b67585d44acb396
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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