tert-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 → HCID 46195463, compound

HRID 710454Notes

Reaction equation

[C:1]12([C:11]3[CH:12]=[C:13]([CH:35]=[CH:36][C:37]=3[O:38][CH:39]([CH3:41])[CH3:40])[CH2:14][CH2:15][N:16]([CH2:18][C:19]3([NH:27]C(=O)OC(C)(C)C)[CH2:24][O:23]C(C)(C)[O:21][CH2:20]3)[CH3:17])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(OC1C=C(C2ON=C(C3C=CC=C4C=3CCN4CC3(NC(=O)OC(C)(C)C)COC(C)(C)OC3)N=2)C=CC=1OCC)C>>[NH2:27][C:19]([CH2:18][N:16]([CH2:15][CH2:14][C:13]1[CH:35]=[CH:36][C:37]([O:38][CH:39]([CH3:41])[CH3:40])=[C:11]([C:1]23[CH2:10][CH:5]4[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]4)[CH2:2]2)[CH2:8]3)[CH:12]=1)[CH3:17])([CH2:24][OH:23])[CH2:20][OH:21]

Participants

Reactant 2

HCID 66726782tert-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

HCID 131733967HCID 131733967, compound

Product 1

HCID 46195463HCID 46195463, compoundYield 49%

Procedure

When the product of Step G was substituted for tert-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 49% yield. 1H-NMR (CDCl3) 1.34 (d, 6H, J=6.00 Hz); 1.73 (s, 6H); 2.03 (s, 3H); 2.08 (s, 6H); 2.4 (s, 3H); 2.51 (s, 2H); 2.66 (s, 4H); 3.42 (d, 2H, J=10.87 Hz); 3.47 (d, 2H, J=10.88 Hz); 4.56-4.61 (m, 1H); 6.72 (d, 1H, J=8.34 Hz); 6.98 (dd, 1H, J=2.12, 8.24 Hz); 6.97 (d, 1H, J=2.12 Hz).

Sources & evidence

ORD record: ord-40915fc17b1945baa327cdc2be9f860e
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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