4-((4-chlorophenyl)((3,7-dimethylbenzo[d]isoxazol-5-yl)amino)methyl)-1-(2,4-dimethoxypyrimidin-5-yl)-5-isopropyl-1H-pyrazole-3-carboxylic acid → 4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-5-(3,7-dimethylbenzo[d]-isoxazol-5-yl)-3-isopropyl-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(2H)-one

HRID 873878Notes

Reaction equation

HRID 873878 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:30][C:31]2[CH:32]=[C:33]([CH3:41])[C:34]3[O:38][N:37]=[C:36]([CH3:39])[C:35]=3[CH:40]=2)[C:9]2[C:10]([C:27]([OH:29])=O)=[N:11][N:12]([C:17]3[C:18]([O:25][CH3:26])=[N:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=3)[C:13]=2[CH:14]([CH3:16])[CH3:15])=[CH:4][CH:3]=1>CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:9]3[C:10](=[N:11][N:12]([C:17]4[C:18]([O:25][CH3:26])=[N:19][C:20]([O:23][CH3:24])=[N:21][CH:22]=4)[C:13]=3[CH:14]([CH3:16])[CH3:15])[C:27](=[O:29])[N:30]2[C:31]2[CH:32]=[C:33]([CH3:41])[C:34]3[O:38][N:37]=[C:36]([CH3:39])[C:35]=3[CH:40]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 1177028274-((4-chlorophenyl)((3,7-dimethylbenzo[d]isoxazol-5-yl)amino)methyl)-1-(2,4-dimethoxypyrimidin-5-yl)-5-isopropyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 862946914-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-5-(3,7-dimethylbenzo[d]-isoxazol-5-yl)-3-isopropyl-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(2H)-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared in analogy to the procedure described in Example 1 using 4-((4-chlorophenyl)((3,7-dimethylbenzo[d]isoxazol-5-yl)amino)methyl)-1-(2,4-dimethoxypyrimidin-5-yl)-5-isopropyl-1H-pyrazole-3-carboxylic acid (Step 46.13). tR: 1.25 min (LC-MS 2); ESI-MS: 559 [M+H]+ (LC-MS 2); Rf=0.50 (EtOAc); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.48 (d, J=6.8 Hz, 3H) 1.17 (d, J=6.7 Hz, 3H) 2.45 (s, 3H) 2.52 (s, 3H) 2.61-2.71 (m, 1H) 3.96 (s, 3H) 4.01 (s, 3H) 6.69 (s, 1H) 7.33-7.42 (m, 4H) 7.67 (s, 1H) 7.84 (d, J=1.5 Hz, 1H) 8.64 (s, 1H).

Sources & evidence

ORD record
ord-003433ef692141ac86c5f20218d320d4
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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