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-((5-(5-(4-propylphenyl)-1,2,4-oxadiazol-3-yl)-3,4-dihydroquinolin-1(2H)-yl)methyl)propane-1,3-diol

HRID 710481Notes

Reaction equation

CC1(C)[O:7][CH2:6][C:5]([NH:33]C(=O)OC(C)(C)C)([CH2:8][N:9]2[C:18]3[C:13](=[C:14]([C:19]4[N:23]=[C:22]([C:24]5[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH3:32])=[CH:26][CH:25]=5)[O:21][N:20]=4)[CH:15]=[CH:16][CH:17]=3)[CH2:12][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>>[NH2:33][C:5]([CH2:8][N:9]1[C:18]2[C:13](=[C:14]([C:19]3[N:23]=[C:22]([C:24]4[CH:25]=[CH:26][C:27]([CH2:30][CH2:31][CH3:32])=[CH:28][CH:29]=4)[O:21][N:20]=3)[CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10]1)([CH2:6][OH:7])[CH2:4][OH:3]

Participants

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-ylcarbamate

HCID 86661812tert-Butyl 2,2-dimethyl-5-((5-(5-(4-propylphenyl)-1,2,4-oxadiazol-3-yl)-3,4-dihydroquinolin-1(2H)-yl)methyl)-1,3-dioxan-5-ylcarbamate

Product 1

HCID 461958842-Amino-2-((5-(5-(4-propylphenyl)-1,2,4-oxadiazol-3-yl)-3,4-dihydroquinolin-1(2H)-yl)methyl)propane-1,3-diolYield 45%

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 45% yield, as colourless solid. 1H-NMR (CDCl3+CD3OD) 0.89 (tr, 3H, J=7.4 Hz); 1.55-1.68 (m, 2H); 1.88 (m, 2H); 2.61 (tr, 2H, J=7.4 Hz); 2.95-3.1 (m, 8H+H2O); 3.31 (m, 4H); 3.35-3.79 (m, 4H); 7.06-7.16 (m, 3H); 7.23-7.29 (m, 2H+CDCl3); 8.02 (d, 2H, J=8 Hz).

Sources & evidence

ORD record: ord-c25f1670aa4e49b69fb01d2d328632a3
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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