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Ethanol → N-(5-(2-aminoquinolin-6-yl)-2-chloropyridin-3-yl)-4-methoxybenzenesulfonamide

HRID 1963786
Notes
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Reaction equation

HRID 1963786 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Cl:7][C:8]1[C:13]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:12][C:11](B2OC(C)(C)C(C)(C)O2)=[CH:10][N:9]=1.Br[C:36]1[CH:37]=[C:38]2[C:43](=[CH:44][CH:45]=1)[N:42]=[C:41]([NH2:46])[CH:40]=[CH:39]2.CCO>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:46][C:41]1[CH:40]=[CH:39][C:38]2[C:43](=[CH:44][CH:45]=[C:36]([C:11]3[CH:12]=[C:13]([NH:14][S:15]([C:18]4[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=4)(=[O:16])=[O:17])[C:8]([Cl:7])=[N:9][CH:10]=3)[CH:37]=2)[N:42]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 111836666-Bromoquinolin-2-amineHCID 57416510N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-methoxybenzenesulfonamide

Product 1

HCID 44610009N-(5-(2-aminoquinolin-6-yl)-2-chloropyridin-3-yl)-4-methoxybenzenesulfonamideYield 12%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A reaction tube was charged with sodium carbonate (353 μl, 706 μmol), Pd(Ph3P)4 (16 mg, 14 μmol), N-(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-4-methoxybenzenesulfonamide (100 mg, 235 μmol), 6-bromoquinolin-2-amine (53 mg, 235 μmol) and 1.2 mL EtOH. The tube was sealed and the mixture was heated at 90° C. for 2 h. The mixture was diluted with CH2Cl2 and washed with water. The organic portion was dried with MgSO4, filtered and concentrated. The crude material was dissolved in MeOH/DMSO and purified by reverse phase chromatography, 10-90% ACN/0.1% TFA in water over 15 min. The aqueous portion was brought to ˜pH 7 and extracted. The organic portion was dried, filtered and concentrated to provide N-(5-(2-aminoquinolin-6-yl)-2-chloropyridin-3-yl)-4-methoxybenzenesulfonamide (12 mg, 12% yield) as a light yellow solid. MS (ESI pos. ion) m/z calc'd for C21H17ClN4O3S: 440.9/442.9; found 441.0/443.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.88 (s, 3 H), 6.88 (br s, 2 H), 6.89 (d, 1 H, J=8), 7.15-7.18 (m, 2 H), 7.61 (d, 1 H, J=8), 7.75-7.80 (m, 3 H), 7.97-8.00 (m, 2 H), 8.03-8.06 (m, 1 H), 8.62-8.63 (m, 1 H), 10.46 (br, s, 1 H).

Workup

  1. customThe tube was sealed
  2. washwashed with water
  3. dry with materialThe organic portion was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe crude material was dissolved in MeOH/DMSO
  7. custompurified by reverse phase chromatography, 10-90% ACN/0.1% TFA in water over 15 min
  8. extractionextracted
  9. customThe organic portion was dried
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-2ea460535f69422a8e1f69bf4a95029d
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08415376B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes