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

Potassium Carbonate → Ethyl 4-[(4-fluorobenzenesulfonyl)methylamino]-1,3-dimethyl-1h-pyrazolo[3,4-b] pyridine-5-carboxylate

HRID 496596
Notes
Print preview

Reaction equation

HRID 496596 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([CH3:17])[N:14]=[C:15]([CH3:16])[C:3]=12.CN[S:20]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)(=[O:22])=[O:21].C([O-])([O-])=O.[K+].[K+].[CH3:36][N:37]1CCCC1=O>C1OCCOCCOCCOCCOCCOC1>[F:29][C:26]1[CH:25]=[CH:24][C:23]([S:20]([CH2:36][NH:37][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]3[N:13]([CH3:17])[N:14]=[C:15]([CH3:16])[C:3]=23)(=[O:21])=[O:22])=[CH:28][CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 24400544-fluoro-N-methylbenzene-1-sulfonamideHCID 2736380ethyl 4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Product 1

HCID 69733699Ethyl 4-[(4-fluorobenzenesulfonyl)methylamino]-1,3-dimethyl-1h-pyrazolo[3,4-b] pyridine-5-carboxylate

Reagents, catalysts & solvents

1
HCID 2855718-Crown-6Catalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 2.53 g (0.01 mol) of ethyl 4-chloro-1,3-dimethyl-1H pyrazolo[3,4-b]pyridine-5-carboxylate, 1.89 g (0.01 mol) of N-methyl-4-fluorobenzenesulfonamide, 6.91 g (0.05 mol) of anhydrous K2CO3, 0.143 g of 18-crown-6 and 70 ml of anhydrous 1-methyl-2-pyrrolidinone was stirred and heated at 100° C. for 17 hours. The solvent was removed under vacuum and water added to the residue. The mixture was extracted with CH2Cl2, and the extract washed with H2O, brine and dried (Na2SO4). The solution was filtered through a pad of hydrous magnesium silicate and the filtrate concentrated to dryness under vacuum to give 4.98 g of an oil. This oil was chromatographed on a silica gel column with ethyl acetate-hexane(2:3) as solvent to give 3.15 g of solid, mp 107-109° C.

Workup

  1. customThe solvent was removed under vacuum and water
  2. additionadded to the residue
  3. extractionThe mixture was extracted with CH2Cl2
  4. washthe extract washed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationThe solution was filtered through a pad of hydrous magnesium silicate
  7. concentrationthe filtrate concentrated to dryness under vacuum

Sources & evidence

ORD record
ord-4b82875573834294837352ec2141a354
Source dataset
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06946473B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes