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 46195322, compound

HRID 710447Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1([CH2:16][N:17]2[C:25]3[C:20](=[CH:21][C:22]([CH2:26][CH2:27][C:28]4[CH:33]=[CH:32][C:31]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=5[C:40]([F:43])([F:42])[F:41])=[CH:30][CH:29]=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]([CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[C:40]([F:43])([F:41])[F:42])=[CH:30][CH:29]=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 131733966HCID 131733966, compound

Product 1

HCID 46195322HCID 46195322, compound

Procedure

When the product of Step E 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 100%. 1H-NMR (CD3OD/CDCl3) 2.8-2.86 (m, 4H); 2.89 (tr, 2H, J=8.29 Hz); 3.0 (s, 2H); 3.39 (tr, 2H, J=8.29 Hz); 3.48 (d, 2H, J=10.88 Hz); 3.55 (d, 2H, J=10.92 Hz); 6.51 (d, 1H, J=8.6 Hz); 6.86-6.88 (m, 2H); 7.14 (m, 3H); 7.17-7.37 (m, 2H); 7.4 (tr, 1H, J=7.57 Hz); 7.5 (tr, 1H, J=7.01 Hz); 7.68 (d, 1H, J=7.77 Hz).

Sources & evidence

ORD record: ord-f025e4fcac2b4c7a81979db04f82cfdc
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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