Hydrochloric Acid → 3-(((1S)-2-Hydroxy-1-methylethyl)oxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-(4-(methylsulfonyl)phenoxy)benzamide

HRID 644096Notes

Reaction equation

C([O:5][CH2:6][C@H:7]([CH3:35])[O:8][C:9]1[CH:10]=[C:11]([CH:21]=[C:22]([O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)[CH:23]=1)[C:12]([NH:14][C:15]1[CH:19]=[CH:18][N:17]([CH3:20])[N:16]=1)=[O:13])(C)(C)C.Cl>CO.C(OC(C)=O)(C)C.O>[OH:5][CH2:6][C@H:7]([CH3:35])[O:8][C:9]1[CH:10]=[C:11]([CH:21]=[C:22]([O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:32])=[O:33])=[CH:27][CH:26]=2)[CH:23]=1)[C:12]([NH:14][C:15]1[CH:19]=[CH:18][N:17]([CH3:20])[N:16]=1)=[O:13]

Participants

Conditions

Temperature: 50 °C

Procedure

To a 25 ml round-bottomed flask was charged 3-[(1S)-2-tert-butoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(methylsulfonyl)phenoxy]benzamide (498.4 μmol, 250.0 mg). This was dissolved in methanol (4 ml) and HCl (4 ml) was added to the flask in one portion. The reaction was heated to 50° C. for 1.5 hours. Solvent was removed in vacuo to yield a colourless solid that quickly changed to liquid form on standing. The liquid was dissolved in iPrOAc (10 ml) and water (10 ml). The aqueous layer was extracted with further iPrOAc (10 ml). The combined organic layer was dried with MgSO4 and the solvent was removed in vacuo to yield crude title product (142 mg; 63.95% yield) as a white foamy solid.

Workup

customSolvent was removed in vacuo
customto yield a colourless solid that
extractionThe aqueous layer was extracted with further iPrOAc (10 ml)
dry with materialThe combined organic layer was dried with MgSO4
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-7d8014b990fc415081854a0c42e613d1
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700640B2

Reaction notes

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