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 46195465, compound

HRID 710459Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1([CH2:16][N:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][C:21]([C:31]45[CH2:40][CH:35]6[CH2:36][CH:37]([CH2:39][CH:33]([CH2:34]6)[CH2:32]4)[CH2:38]5)=[C:22]([O:27][CH:28]([CH3:30])[CH3:29])[CH:23]=3)[CH2:18]2)[CH2:13][O:12]C(C)(C)[O:10][CH2:9]1)(C)(C)C.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>>[NH2:7][C:8]([CH2:16][N:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][C:21]([C:31]34[CH2:38][CH:37]5[CH2:39][CH:33]([CH2:34][CH:35]([CH2:36]5)[CH2:40]3)[CH2:32]4)=[C:22]([O:27][CH:28]([CH3:30])[CH3:29])[CH:23]=2)[CH2:18]1)([CH2:13][OH:12])[CH2:9][OH:10]

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 131733968HCID 131733968, compound

Product 1

HCID 46195465HCID 46195465, compoundYield 77%

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 77% yield, as pale paste. 1H-NMR (CDCl3) 1.26 (d, 6H, J=6.07 Hz); 1.65 (m, 6H); 1.94 (m, 3H); 1.67 (m, 6H); 2.52 (m, 2H); 2.75 (m, 4H); 3.38-3.47 (m, 4H); 3.59 (s, 2H); 4.48-4.52 (m, 1H); 6.46 (s, 1H); 6.72 (s, 1H).

Sources & evidence

ORD record: ord-b99dea3d8adf4c079276d7c6222830ee
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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