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

HRID 710373Notes

Reaction equation

[CH2:1]([O:3][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[O:10][CH2:11][CH3:12])[CH3:2].CC1(C)OCC(NC(=O)OCCCC)(CNC2C=CC(CCCCCCCC)=CC=2)CO1>>[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]([O:10][CH2:11][CH3:12])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=4)[O:17][N:16]=3)[CH:26]=[CH:25][CH:24]=2)[CH2:20][CH2:21]1)([CH2:29][OH:30])[CH2:33][OH:32]

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 68407657Butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamate

Product 1

HCID 452556482-Amino-2-((4-(5-(3,4-diethoxyphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)propane-1,3-diolYield 71%

Procedure

When the product of Step D was substituted for tea-butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamate in Example 1, Step B, the identical process afforded the title compound in 71% yield, as a creamy solid. 1H-NMR (CDCl3) 1.5 (m, 6H); 1.82 (broad s, 4H+H2O); 3.16 (m, 2H); 3.41-3.59 (m, 8H); 4.13-4.3 (m, 4H); 6.96 (d, 1H, J=7.9 Hz); 7.2 (tr, 1H, J=7.9 Hz); 7.5 (d, 1H, 7.8 Hz); 7.67 (d, 1H, J=1.9 Hz); 7.7 (dd, 1H, J=1.9, 8.4 Hz).

Sources & evidence

ORD record: ord-25f3c68a108d445bb98efd41346bba56
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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