1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (3-Dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenyl}butanoic acid 4-(3-methyl-[1,2,4]oxadiazol-5-yl)phenyl ester

HRID 423275Notes

Reaction equation

HRID 423275 reaction equation
CC1N=C(C2C=CC(O)=CC=2)ON=1.[CH3:14][N:15]([CH3:49])[C:16]([C:18]1[CH:19]=[C:20](CCCC(O)=O)[CH:21]=[CH:22][C:23]=1[NH:24][C:25]([C:27]1[C:28]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:26])=[O:17].CCN=C=NCCCN(C)C.[CH3:61][C:62]1[N:66]=[C:65]([C:67]2[CH:72]=[CH:71][C:70]([O:73][C:74](=[O:108])[CH2:75][CH2:76][CH2:77]C3C=CC(NC(C4C(C5C=CC(C(F)(F)F)=CC=5)=CC=CC=4)=O)=C(C(=O)N(C)C)C=3)=[CH:69][CH:68]=2)[O:64][N:63]=1>>[CH3:61][C:62]1[N:66]=[C:65]([C:67]2[CH:72]=[CH:71][C:70]([O:73][C:74](=[O:108])[CH:75]([C:20]3[CH:21]=[CH:22][C:23]([NH:24][C:25]([C:27]4[C:28]([C:33]5[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:40])[F:41])=[CH:35][CH:34]=5)=[CH:29][CH:30]=[CH:31][CH:32]=4)=[O:26])=[C:18]([C:16](=[O:17])[N:15]([CH3:14])[CH3:49])[CH:19]=3)[CH2:76][CH3:77])=[CH:69][CH:68]=2)[O:64][N:63]=1

Participants

5

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 36924074-(3-Methyl-1,2,4-oxadiazol-5-yl)phenolHCID 116288844-{3-Dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenyl}butanoic acid 4-(3-methyl-[1,2,4]oxadiazol-5-yl)phenyl esterHCID 666763664-{3-Dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenyl}butanoic acid

Product 1

HCID 131729408(3-Dimethylcarbamoyl-4-[(4'-trifluoromethylbiphenyl-2-carbonyl)amino]phenyl}butanoic acid 4-(3-methyl-[1,2,4]oxadiazol-5-yl)phenyl ester

Procedure

4-(3-Methyl-[1,2,4]oxadiazol-5-yl)phenol (64 mg) and 4-{3-dimethylcarbamoyl-4-[(4′-trifluoromethylbiphenyl-2-carbonyl)amino]phenyl}butanoic acid (200 mg)(synthesized separately in a similar manner to Working Example 1-1) were treated (WSC condensation) in a similar manner to Step g) of Working Example 1-1 to give the title compound (Compound 1-2) (112 mg).

Workup

  1. additionwere treated

Sources & evidence

ORD record
ord-fcd7558291c34305afa4e31714576790
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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