tert-Butyl 2,2-dimethyl-5-((4-(5-(6-propylpyridin-3-yl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)-1,3-dioxan-5-ylcarbamate → 2-Amino-2-((4-octylindolin-1-yl)methyl)propane-1,3-diol

HRID 710486Notes

Reaction equation

HRID 710486 reaction equation
CC1(C)[O:7][CH2:6][C:5]([NH:26]C(=O)OC(C)(C)C)([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)[CH2:4][O:3]1.CC1(C)OCC(NC(=O)OC(C)(C)C)(CN2C3C(=C(C4N=C(C5C=NC(CCC)=CC=5)ON=4)C=CC=3)CC2)CO1>>[NH2:26][C:5]([CH2:8][N:9]1[C:17]2[C:12](=[C:13]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)([CH2:6][OH:7])[CH2:4][OH:3]

Participants

3

Reactant 2

HCID 66726785tert-Butyl 2,2-dimethyl-5-((4-(5-(6-propylpyridin-3-yl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)-1,3-dioxan-5-ylcarbamateHCID 86661817tert-Butyl 2,2-dimethyl-5-((4-octylindolin-1-yl)methyl)-1,3-dioxan-5-ylcarbamate

Product 1

HCID 461958862-Amino-2-((4-octylindolin-1-yl)methyl)propane-1,3-diolYield 68%

Procedure

When the product of Step E was substituted for tert-butyl 2,2-dimethyl-5-((4-(5-(6-propylpyridin-3-yl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)-1,3-dioxan-5-ylcarbamate in Example 66, Step F, the identical process afforded the title compound in 68% yield, as colourless solid. 1H-NMR (CDCl3) 0.86 (m, 3H); 1.28 (m, 10H); 1.53 (m, 2H); 1.8 (broad s, 4H+H2O); 2.48 (tr, 2H, J=7.6 Hz); 2.93 (tr, 2H, J=8.2 Hz); 3.08 (s, 2H); 3.46 (tr, 2H, J=8.7 Hz); 3.58 (m, 4H); 6.46 (d, 1H, J=7.8 Hz); 6.53 (d, 1H, J=7.6 Hz); 7.01 (m, 1H).

Sources & evidence

ORD record
ord-21f011f6bd52418bab6312d01945af20
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

Loading…