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Sodium 1-Methyl 3-Sulfinopropionate → 3-[5-(1-{[1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-cyclopropyl)-pyridine-2-sulfonyl]-propionic acid methyl ester

HRID 2172979
Notes
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Reaction equation

HRID 2172979 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([C:8]2([NH:11][C:12]([C:14]3[C:15]4[CH:22]=[N:21][N:20]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=5)[C:16]=4[CH:17]=[N:18][CH:19]=3)=[O:13])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:30][O:31][C:32](=[O:38])[CH2:33][CH2:34][S:35]([O-:37])=[O:36].[Na+]>CS(C)=O.[Cu]I>[CH3:30][O:31][C:32](=[O:38])[CH2:33][CH2:34][S:35]([C:2]1[CH:3]=[CH:4][C:5]([C:8]2([NH:11][C:12]([C:14]3[C:15]4[CH:22]=[N:21][N:20]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=5)[C:16]=4[CH:17]=[N:18][CH:19]=3)=[O:13])[CH2:10][CH2:9]2)=[CH:6][N:7]=1)(=[O:37])=[O:36]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 23665669Sodium 1-Methyl 3-SulfinopropionateHCID 529167991-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [1-(6-bromo-pyridin-3-yl)-cyclopropyl]-amide

Product 1

HCID 529174263-[5-(1-{[1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-cyclopropyl)-pyridine-2-sulfonyl]-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid [1-(6-bromo-pyridin-3-yl)-cyclopropyl]-amide (0.250 g, 0.553 mmol), sodium 3-methoxy-3-oxopropane-1-sulfinate (289 mg, 1.66 mmol) and copper (I) iodide (316 mg, 1.66 mmol) in DMSO (2 mL) is placed in a microwave tube and evacuated and purged with argon three times. The reaction mixture is heated in a microwave at 110° C. for 2 hours, diluted with ethyl acetate (200 mL), washed with saturated aqueous ammonium chloride (4×100 mL), saturated aqueous sodium bicarbonate (100 mL), brine (100 mL), dried over MgSO4, filtered and concentrated. The resulting residue is purified by silica gel chromatography eluting with a gradient of 50-100% ethyl acetate in heptane to afford the title compound as a solid.

Workup

  1. customevacuated
  2. custompurged with argon three times
  3. additiondiluted with ethyl acetate (200 mL)
  4. washwashed with saturated aqueous ammonium chloride (4×100 mL), saturated aqueous sodium bicarbonate (100 mL), brine (100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue is purified by silica gel chromatography
  9. washeluting with a gradient of 50-100% ethyl acetate in heptane

Sources & evidence

ORD record
ord-e61f11fda3cf4c0c9a225c6d3e119664
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09056858B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes