3-({5-Chloro-3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carbonyl}-isopropyl-amino)-pyrazole-1-carboxylic acid tert-butyl ester → HCID 178457751, compound

HRID 419188Notes

Reaction equation

C(OC([N:8]1[CH:12]=[CH:11][C:10]([N:13]([C:17]([C:19]2[C:24]([N:25]([S:29]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([C:39]([F:42])([F:41])[F:40])[CH:33]=3)(=[O:31])=[O:30])COC)=[CH:23][C:22]([Cl:43])=[CH:21][N:20]=2)=[O:18])[CH:14]([CH3:16])[CH3:15])=[N:9]1)=O)(C)(C)C>Cl.O1CCOCC1.O>[CH:14]([N:13]([C:10]1[CH:11]=[CH:12][NH:8][N:9]=1)[C:17]([C:19]1[C:24]([NH:25][S:29]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([C:39]([F:42])([F:41])[F:40])[CH:33]=2)(=[O:30])=[O:31])=[CH:23][C:22]([Cl:43])=[CH:21][N:20]=1)=[O:18])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 85 °C

Procedure

3-({5-chloro-3-[(4-chloro-3-trifluoromethyl-benzenesulfonyl)-methoxymethyl-amino]-pyridine-2-carbonyl}-isopropyl-amino)-pyrazole-1-carboxylic acid tert-butyl ester from step 2 was dissolved in a mixture of 4 M HCl in dioxane (4 mL) and water (1 mL), heated to 85° C. for 2 h. The solvent was evaporated and the residue was purified with HPLC to give 5-chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridine-2-carboxylic acid isopropyl-(1H-pyrazol-3-yl)-amide. MS m/z: 522 (M+H)+.

Workup

customThe solvent was evaporated
customthe residue was purified with HPLC

Sources & evidence

ORD record: ord-f993fed5d85a448dadd9b42a408be839
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093247B2

Reaction notes

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