HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 644096
Notes
Print preview

Reaction equation

HRID 644096 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 115551333-[(1S)-2-tert-butoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(methylsulfonyl)phenoxy]benzamide

Product 1

HCID 115251163-(((1S)-2-Hydroxy-1-methylethyl)oxy)-N-(1-methyl-1H-pyrazol-3-yl)-5-(4-(methylsulfonyl)phenoxy)benzamideYield 64%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent
HCID 962
Water
Solvent
HCID 7915Isopropyl AcetateSolvent

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

  1. customSolvent was removed in vacuo
  2. customto yield a colourless solid that
  3. extractionThe aqueous layer was extracted with further iPrOAc (10 ml)
  4. dry with materialThe combined organic layer was dried with MgSO4
  5. 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

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes