5-Amino-3-methylbenzo[d]isoxazole → ethyl 4-((4-chlorophenyl)(3-methylbenzo[d]isoxazol-5-ylamino)methyl)-1,5-dimethyl-1H-pyrazole-3-carboxylate

HRID 873847Notes

Reaction equation

HRID 873847 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]2[C:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:11][N:12]([CH3:15])[C:13]=2[CH3:14])=[CH:4][CH:3]=1.[CH3:22][C:23]1[C:27]2[CH:28]=[C:29]([NH2:32])[CH:30]=[CH:31][C:26]=2[O:25][N:24]=1>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:32][C:29]2[CH:30]=[CH:31][C:26]3[O:25][N:24]=[C:23]([CH3:22])[C:27]=3[CH:28]=2)[C:9]2[C:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:11][N:12]([CH3:15])[C:13]=2[CH3:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 213453975-Amino-3-methylbenzo[d]isoxazoleHCID 117702851ethyl 4-((4-chlorophenyl)(hydroxy)methyl)-1,5-dimethyl-1H-pyrazole-3-carboxylate

Product 1

HCID 117703133ethyl 4-((4-chlorophenyl)(3-methylbenzo[d]isoxazol-5-ylamino)methyl)-1,5-dimethyl-1H-pyrazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared in analogy to the procedure described in Step 1.4 using ethyl 4-((4-chlorophenyl)(hydroxy)methyl)-1,5-dimethyl-1H-pyrazole-3-carboxylate (Step 28.2) and 3-methylbenzo[d]isoxazol-5-amine (Step 33.3). tR: 5.40 min (HPLC 1); tR: 1.20 min (LC-MS 2); ESI-MS: 439 [M+H]+ (LC-MS 2); Rf=0.77 (CH2Cl2/MeOH 9:1).

Sources & evidence

ORD record
ord-afa2c91e17684b95ba176a6866d4cde7
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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