[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid → 2-[3-(4-Chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[3-hydroxy-1-(3-methoxyphenyl)propyl]acetamide

HRID 220702Notes

Reaction equation

HRID 220702 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C@H:14](O)[C:15](F)(F)F)[C:11](=[O:20])[N:10]([CH2:21][C:22]([NH:24][CH:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3C)[CH2:26][CH2:27][OH:28])=[O:23])[N:9]=2)=[CH:4][CH:3]=1.ClC1C=CC(C2N(C3CC3)[C:46](=[O:51])N(CC(O)=O)N=2)=CC=1.NC(C1C=CC=C(OC)C=1)CCO>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:14][CH2:15]3)[C:11](=[O:20])[N:10]([CH2:21][C:22]([NH:24][CH:25]([C:29]3[CH:30]=[CH:31][CH:32]=[C:33]([O:51][CH3:46])[CH:34]=3)[CH2:26][CH2:27][OH:28])=[O:23])[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 42632357[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acidHCID 43817658HCID 43817658, compoundHCID 59536857HCID 59536857, compound

Product 1

HCID 469280752-[3-(4-Chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[3-hydroxy-1-(3-methoxyphenyl)propyl]acetamide

Procedure

In the same way as for the compound from Example 86, 30 mg (0.10 mmol) of [3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acid (for preparation see WO 2007/134862, Example 88A) and 20 mg (0.11 mmol) of 3-amino-3-(3-methoxyphenyl)propan-1-ol were reacted. This gave 30 mg (63% of theory) of the target compound.

Sources & evidence

ORD record
ord-20dab0949fb640aca90136007974ec8e
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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