4-(((5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)amino)(4-chlorophenyl)methyl)-1-cyclopropyl-5-(trifluoromethyl)-1H-pyrazole-3-carboxylic acid → 5-(5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-(4-chlorophenyl)-2-cyclopropyl-3-(trifluoromethyl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(2H)-one

HRID 873862Notes

Reaction equation

HRID 873862 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[N:6]([CH3:9])[CH:5]=[C:4]([NH:10][CH:11]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[C:12]2[C:13]([C:24](O)=[O:25])=[N:14][N:15]([CH:21]3[CH2:23][CH2:22]3)[C:16]=2[C:17]([F:20])([F:19])[F:18])[CH:3]=1>C(Cl)Cl>[Cl:1][C:2]1[C:7](=[O:8])[N:6]([CH3:9])[CH:5]=[C:4]([N:10]2[CH:11]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)[C:12]3[C:13](=[N:14][N:15]([CH:21]4[CH2:22][CH2:23]4)[C:16]=3[C:17]([F:20])([F:18])[F:19])[C:24]2=[O:25])[CH:3]=1

Participants

3

Reactant 1

HCID 1177026994-(((5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)amino)(4-chlorophenyl)methyl)-1-cyclopropyl-5-(trifluoromethyl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 862944805-(5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-4-(4-chlorophenyl)-2-cyclopropyl-3-(trifluoromethyl)-4,5-dihydropyrrolo[3,4-c]pyrazol-6(2H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared in analogy to the procedure described in Example 1 using 4-(((5-chloro-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)amino)(4-chlorophenyl)methyl)-1-cyclopropyl-5-(trifluoromethyl)-1H-pyrazole-3-carboxylic acid (Step 40.4) at RT for 30 min. tR: 1.12 min (LC-MS 2); ESI-MS: 483 [M+H]+ (LC-MS 2); Rf=0.69 (CH2Cl2/5% MeOH/1% ammonia); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.11-1.22 (m, 2H) 1.22-1.38 (m, 2H) 3.41 (s, 3H) 3.86-4.00 (m, 1H) 6.36 (s, 1H) 7.26 (m, J=8.6 Hz, 2H) 7.36 (m, J=8.6 Hz, 2H) 7.90 (d, J=2.7 Hz, 1H) 7.87 (d, J=2.7 Hz, 1H).

Sources & evidence

ORD record
ord-1bbfed00d3174ffead48aa8eec404f4f
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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