tert-Butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamate → 2-Amino-2-((5-((4,6-dichlorobenzofuran-2-yl)methoxy)indolin-1-yl)methyl)propane-1,3-diol

HRID 710305Notes

Reaction equation

HRID 710305 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH2:11][O:12][C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[N:18]([CH2:22][C:23]3([NH:31]C(=O)OC(C)(C)C)[CH2:28][O:27]C(C)(C)[O:25][CH2:24]3)[CH2:17][CH2:16]4)[O:10][C:6]=2[CH:5]=[C:4]([Cl:39])[CH:3]=1.CC1(C)OCC(NC(=O)OC(C)(C)C)(CNC2C=CC(CCCCCCCC)=CC=2)CO1>>[NH2:31][C:23]([CH2:22][N:18]1[C:19]2[C:15](=[CH:14][C:13]([O:12][CH2:11][C:9]3[O:10][C:6]4[CH:5]=[C:4]([Cl:39])[CH:3]=[C:2]([Cl:1])[C:7]=4[CH:8]=3)=[CH:21][CH:20]=2)[CH2:16][CH2:17]1)([CH2:24][OH:25])[CH2:28][OH:27]

Participants

3

Reactant 2

HCID 66726563tert-Butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamateHCID 86661762tert-Butyl 5-((5-((4,6-dichlorobenzofuran-2-yl)methoxy)indolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Product 1

HCID 461948842-Amino-2-((5-((4,6-dichlorobenzofuran-2-yl)methoxy)indolin-1-yl)methyl)propane-1,3-diolYield 37%

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 37% yield, as a off white solid. 1H-NMR (CD3OD) 2.9 (tr, 2H, J=8.2 Hz); 3.37 (tr, 2H, J=8.2 Hz); 3.43-3.53 (m, 4H); 5.0 (s, 2H); 6.5 (d, 1H, J=8.4 Hz); 6.65-6.7 (m, 1H); 6.76 (s, 2H); 7.19 (d, 1H, J=1.5 Hz); 7.37 (m, 1H).

Sources & evidence

ORD record
ord-f389b68265054be980bb3f25c028067a
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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