Methyl-1-(4-((5-chlorobenzofuran-3-yl)methoxy)benzyl)azetidine-3-carboxylate → 1-((4'-(((4-Fluorophenyl)(isopropyl)amino)methyl)biphenyl-4-yl)methyl)azetidine-3-carboxylic acid

HRID 717666Notes

Reaction equation

HRID 717666 reaction equation
C[O:2][C:3]([CH:5]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][N:23]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[CH:24]([CH3:26])[CH3:25])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:6]1)=[O:4].COC(C1CN(CC2C=CC(OCC3C4C=C(Cl)C=CC=4OC=3)=CC=2)C1)=O>>[F:33][C:30]1[CH:31]=[CH:32][C:27]([N:23]([CH2:22][C:19]2[CH:20]=[CH:21][C:16]([C:13]3[CH:14]=[CH:15][C:10]([CH2:9][N:7]4[CH2:6][CH:5]([C:3]([OH:4])=[O:2])[CH2:8]4)=[CH:11][CH:12]=3)=[CH:17][CH:18]=2)[CH:24]([CH3:25])[CH3:26])=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 66614996Methyl-1-(4-((5-chlorobenzofuran-3-yl)methoxy)benzyl)azetidine-3-carboxylateHCID 66615206Methyl-1-((4'-(((4-fluorophenyl)(isopropyl)amino)methyl)biphenyl-4-yl)methyl)azetidine-3-carboxylate

Product 1

HCID 461996731-((4'-(((4-Fluorophenyl)(isopropyl)amino)methyl)biphenyl-4-yl)methyl)azetidine-3-carboxylic acidYield 60%

Procedure

When the product of Step A was substituted for methyl-1-(4-((5-chlorobenzofuran-3-yl)methoxy)benzyl)azetidine-3-carboxylate in Example 25, Step E, the similar process afforded the title compound in 60% yield, as creamy solid. 1H-NMR (CDCl3+CD3OD) 7.66 (d, 2H, J=8.13 Hz); 7.62-7.57 (m, 4H); 7.41 (d, 2H, J=8.07 Hz); 6.95-6.85 (m, 2H); 6.85-6.75 (m, 2H); 4.44 (s, 2H); 4.39 (s, 2H); 4.39-4.2 (m, 2H); 3.5-3.45 (m, 1H); 1.26 (d, 6H, J=6.54 Hz).

Sources & evidence

ORD record
ord-7c46e92c53a843f68e9a9aeff1413824
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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