tert-Butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamate → 2-Amino-2-((5-(5-(3-chloro-4-methoxyphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)propane-1,3-diol

HRID 710299Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH2:24][C:25]3([NH:33]C(=O)OC(C)(C)C)[CH2:30][O:29]C(C)(C)[O:27][CH2:26]3)[CH2:19][CH2:18]4)[N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].CC1(C)OCC(NC(=O)OC(C)(C)C)(CNC2C=CC(CCCCCCCC)=CC=2)CO1>>[NH2:33][C:25]([CH2:24][N:20]1[C:21]2[C:17](=[CH:16][C:15]([C:12]3[N:11]=[C:10]([C:4]4[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=4)[O:14][N:13]=3)=[CH:23][CH:22]=2)[CH2:18][CH2:19]1)([CH2:26][OH:27])[CH2:30][OH:29]

Participants

Reactant 2

HCID 66726563tert-Butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamate

HCID 86661761tert-Butyl 5-((5-(5-(3-chloro-4-methoxyphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Product 1

HCID 461947462-Amino-2-((5-(5-(3-chloro-4-methoxyphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)propane-1,3-diolYield 67%

Procedure

When the product of Step G was substituted for tert-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 67% yield, as a creamy solid. 1H-NMR (CDCl3) 1.54 (broad s, 4H+H2O); 3.07 (m, 2H); 3.19 (s, 2H); 3.47 (s, 2H); 3.55-3.62 (m, 6H); 3.98 (s, 3H); 6.67 (m, 1H); 7.03 (m, 1H); 7.82-7.9 (m, 2H); 8.01-8.06 (m, 1H); 8.22 (s, 1H); 1H-NMR (DMSO-d6) 1.52 (m, 2H); 2.9-3.03 (m, 4H); 3.57 (tr, 2H, J=8.6 Hz); 3.95 (s, 3H); 4.6 (s, 2H); 6.66 (d, 1H, J=8.4 Hz); 7.36 (d, 1H, J=8.4 Hz); 7.62-7.7 (m, 2H); 8.05-8.11 (m, 2H).

Sources & evidence

ORD record: ord-42ed18c24f114cb685d14671caeca28e
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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