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

HRID 710378Notes

Reaction equation

CC1(C)[O:7][CH2:6][C:5]([NH:39]C(=O)OC(C)(C)C)([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([C:18]4[N:22]=[C:21]([C:23]5[CH:28]=[CH:27][C:26]([C:29]6[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=6[C:35]([F:38])([F:37])[F:36])=[CH:25][CH:24]=5)[O:20][N:19]=4)[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)(CNC2C=CC(CCCCCCCC)=CC=2)CO1>>[NH2:39][C:5]([CH2:8][N:9]1[C:17]2[C:12](=[C:13]([C:18]3[N:22]=[C:21]([C:23]4[CH:28]=[CH:27][C:26]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=5[C:35]([F:38])([F:37])[F:36])=[CH:25][CH:24]=4)[O:20][N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)([CH2:4][OH:3])[CH2:6][OH:7]

Participants

Reactant 2

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

HCID 86661785tert-Butyl 2,2-dimethyl-5-((4-(5-(2'-(trifluoromethyl)biphenyl-4-yl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)-1,3-dioxan-5-ylcarbamate

Product 1

HCID 667268342-Amino-2-((4-(5-(2'-(trifluoromethyl)biphenyl-4-yl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)propane-1,3-diolYield 71%

Procedure

When the product of Step E 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 71% yield, as a creamy solid. 1H-NMR (CD3OD+CDCl3) 3.1 (s, 2H); 3.35-3.6 (m, 8H); 4.1 (HDO); 6.76 (d, 1H, J=7.8 Hz); 7.17 (tr, 1H, J=7.8 Hz); 7.33 (tr, 1H, J=7.5 Hz); 7.41-7.51 (m, 4H); 7.57 (tr, 1H, J=7.3 Hz); 8.19 (d, 2H, J=8.3 Hz).

Sources & evidence

ORD record: ord-1d50eac5b5c44ea1a99a9fe0ba2a18ed
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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