1-{4'-[1-methyl-5-((R)-1-phenyl-ethoxycarbonylamino)-1H-[1,2,3]triazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid → 1-{4'-[3-Methyl-5-((R)-1-phenyl-ethoxycarbonylamino)-3H-[1,2,3]triazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid

HRID 631920Notes

Reaction equation

HRID 631920 reaction equation
C[N:2]1[C:6]([NH:7][C:8]([O:10][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])=[O:9])=[C:5]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4([C:34]([OH:36])=[O:35])[CH2:33][CH2:32]4)=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)[N:4]=[N:3]1.Br[C:38]1C=CC(C2N(C)N=NC=2C(O)=O)=CC=1>>[CH3:38][N:4]1[C:5]([C:19]2[CH:20]=[CH:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4([C:34]([OH:36])=[O:35])[CH2:33][CH2:32]4)=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)=[C:6]([NH:7][C:8]([O:10][C@@H:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH3:12])=[O:9])[N:2]=[N:3]1

Participants

3

Reactant 2

HCID 708562661-{4'-[1-methyl-5-((R)-1-phenyl-ethoxycarbonylamino)-1H-[1,2,3]triazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acidHCID 712662725-(4-bromo-phenyl)-1-methyl-1H-[1,2,3]triazole-4-carboxylic acid

Product 1

HCID 712664711-{4'-[3-Methyl-5-((R)-1-phenyl-ethoxycarbonylamino)-3H-[1,2,3]triazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid

Procedure

This compound was prepared using the same method as described for the preparation of 1-{4′-[1-methyl-5-((R)-1-phenyl-ethoxycarbonylamino)-1H-[1,2,3]triazol-4-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid in Example 2, except that 5-(4-bromo-phenyl)-1-methyl-1H-[1,2,3]triazole-4-carboxylic acid (from step 4b in Example 1) was used. LC/MS calcd for C28H26N4O4 (m/e) 482.0, obsd 483.0 (M+H); 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.15-1.30 (m, 2.4H), 1.32-1.62 (m, 4.6H), 4.05 (s, 3H), 5.69 (br m, 1H), 7.20-7.40 (br m, 5H), 7.46 (d, J=8.1 Hz, 2H), 7.59 (d, J=−8.1 Hz, 2H), 7.66 (d, J=8.1 Hz, 2H), 7.77 (d, J=7.6 Hz, 2H), 9.34 (br s, 1H), 12.39 (s, 1H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-b679656ec84f4c3282d0c2eb94e5ea63
Source dataset
uspto-grants-2016_04
Patent number
US09321738B2

Reaction notes

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