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 46195319, compound

HRID 710439Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1([CH2:16][N:17]2[C:25]3[C:20](=[C:21]([C:26]4[N:30]=[C:29]([C:31]56[CH2:40][CH:35]7[CH2:36][CH:37]([CH2:39][CH:33]([CH2:34]7)[CH2:32]5)[CH2:38]6)[O:28][N:27]=4)[CH:22]=[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](=[C:21]([C:26]3[N:30]=[C:29]([C:31]45[CH2:40][CH:35]6[CH2:34][CH:33]([CH2:39][CH:37]([CH2:36]6)[CH2:38]4)[CH2:32]5)[O:28][N:27]=3)[CH:22]=[CH:23][CH:24]=2)[CH2:19][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 131733965HCID 131733965, compound

Product 1

HCID 46195319HCID 46195319, compoundYield 78%

Procedure

When the product of Step C 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 78% yield. 1H-NMR (DMSO-d6) 1.75 (s, 6H); 2.07 (s, 9H); 2.97-3.57 (m, 12H); 6.7 (d, 1H, J=7.6 Hz); 7.12 (tr, 1H); 7.34 (d, 1H, J=7.7 Hz).

Sources & evidence

ORD record: ord-929fb778ebb14d6098068b2c72639aaf
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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