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 46195745, compound

HRID 710422Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1([CH2:16][N:17]2[C:25]3[C:20](=[CH:21][C:22]([C:26]4[N:30]=[C:29]([C:31]5[CH:36]=[CH:35][C:34]([O:37][CH:38]([CH3:40])[CH3:39])=[C:33]([Cl:41])[CH:32]=5)[O:28][N:27]=4)=[CH:23][CH:24]=3)[CH2:19][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[C:25]2[C:20](=[CH:21][C:22]([C:26]3[N:30]=[C:29]([C:31]4[CH:36]=[CH:35][C:34]([O:37][CH:38]([CH3:39])[CH3:40])=[C:33]([Cl:41])[CH:32]=4)[O:28][N:27]=3)=[CH:23][CH:24]=2)[CH2:19][CH2:18]1)([CH2:9][OH:10])[CH2:13][OH:12]

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 131733960HCID 131733960, compound

Product 1

HCID 46195745HCID 46195745, compoundYield 40%

Procedure

When the product of Step D 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 40% yield, as a fluffy white solid. 1H-NMR (DMSO-d6) 1.32 (d, 6H, J=5.54 Hz); 2.99 (s, 2H), 3.29 (m, 6H); 3.53 (m, 2H); 4.58 (m, 2H); 6.77 (d, 1H, J=7.46 Hz), 7.13 (tr, 1H), 7.24 (d, 1H, J=7.47 Hz), 7.39 (d, 1H, J=8.7 Hz), 7.82-7.84 (m, 1H); 8.05 (d, 1H, J=7.75 Hz); 8.12 (s, 1H).

Sources & evidence

ORD record: ord-2c3c1b3f9adf475a8f790054f23898f3
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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