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-(3,4-dipropylphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)propane-1,3-diol

HRID 710410Notes

Reaction equation

[CH2:1]([C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH2:20][CH2:21][N:22]4[CH2:27][C:28]3([NH:36]C(=O)OC(C)(C)C)[CH2:33][O:32]C(C)(C)[O:30][CH2:29]3)[N:14]=2)[CH:7]=[CH:8][C:9]=1[CH2:10][CH2:11][CH3:12])[CH2:2][CH3:3].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>>[NH2:36][C:28]([CH2:27][N:22]1[C:23]2[C:19](=[C:18]([C:15]3[N:14]=[C:13]([C:6]4[CH:7]=[CH:8][C:9]([CH2:10][CH2:11][CH3:12])=[C:4]([CH2:1][CH2:2][CH3:3])[CH:5]=4)[O:17][N:16]=3)[CH:26]=[CH:25][CH:24]=2)[CH2:20][CH2:21]1)([CH2:33][OH:32])[CH2:29][OH:30]

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 86661796tert-Butyl 5-((4-(5-(3,4-dipropylphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Product 1

HCID 461956062-Amino-2-((4-(5-(3,4-dipropylphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)propane-1,3-diolYield 80%

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 80% yield, as a creamy solid. 1H-NMR (DMSO-d6) 0.94-0.97 (m, 6H); 1.33 (s, 2H); 1.53-1.62 (m, 4H); 2.61-2.68 (m, 4H); 2.98 (s, 2H); 3.2-3.3 (m, 6H, +H2O); 3.54 (tr, 2H, J=9 Hz); 4.55 (m, 2H); 6.77 (d, 1H, J=6 Hz); 7.1-7.16 (m, 1H); 7.25 (d, 1H, J=6 Hz); 7.87-7.91 (m, 2H).

Sources & evidence

ORD record: ord-1fec3f30ba8d43f6bc7a3fc33162600d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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