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 → 2-Amino-2-((4-(5-(3-iodo-4-propoxyphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)propane-1,3-diol

HRID 710403Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH2:19][CH2:20][N:21]4[CH2:26][C:27]3([NH:35]C(=O)OC(C)(C)C)[CH2:32][O:31]C(C)(C)[O:29][CH2:28]3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH3:11].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>>[NH2:35][C:27]([CH2:26][N:21]1[C:22]2[C:18](=[C:17]([C:14]3[N:13]=[C:12]([C:4]4[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][CH3:11])=[C:2]([I:1])[CH:3]=4)[O:16][N:15]=3)[CH:25]=[CH:24][CH:23]=2)[CH2:19][CH2:20]1)([CH2:28][OH:29])[CH2:32][OH:31]

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 86661794tert-Butyl 5-((4-(5-(3-iodo-4-propoxyphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Product 1

HCID 461956042-Amino-2-((4-(5-(3-iodo-4-propoxyphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)propane-1,3-diolYield 75%

Procedure

When the product of Step F 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 75% yield., as a colourless solid. 1H-NMR (DMSO-d6) 1.02 (tr, 3H, J=7.3 Hz); 1.4 (broad s, 2H); 1.72-1.8 (m, 2H); 2.98 (s, 2H); 3.2-3.4 (m, 6H+H2O); 3.53 (tr, 2H, J=8.3 Hz); 4.09 3.53 (tr, 2H, J=6.1 Hz); 4.56 (broad s, 2H); 6.76 (d, 1H, J=7.7 Hz); 7.09-7.25 (m, 3H); 8.1 (d, 1H, J=8.8 Hz); 8.44 (s, 1H).

Sources & evidence

ORD record: ord-8138eb2a583742f5a53989b1d6547c6c
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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