[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-[1-(2-chlorophenyl)-3-hydroxypropyl]acetamide

HRID 220701Notes

Reaction equation

HRID 220701 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([NH:12][C:13](=[O:35])[CH2:14][N:15]1[C:19](=[O:20])[N:18]([CH2:21][C@H:22](O)[C:23](F)(F)F)[C:17]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)=[N:16]1)[CH2:9][CH2:10][OH:11].ClC1C=CC(C2N(C3CC3)C(=O)N(CC(O)=O)N=2)=CC=1>>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([C:17]2[N:18]([CH:21]3[CH2:23][CH2:22]3)[C:19](=[O:20])[N:15]([CH2:14][C:13]([NH:12][CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH2:9][CH2:10][OH:11])=[O:35])[N:16]=2)=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 42632357[3-(4-chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetic acidHCID 59536759N-[1-(2-Chlorophenyl)-3-hydroxypropyl]-2-{3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetamide

Product 1

HCID 595367732-[3-(4-Chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-N-[1-(2-chlorophenyl)-3-hydroxypropyl]acetamide

Procedure

In the same way as for the compound from Example 82, 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) were reacted. This gave 14 mg (30% of theory) of the target compound.

Sources & evidence

ORD record
ord-26f25701642940d88621484437bee8b2
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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