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2,2,2-Cryptand → N-[[3-fluoro-4-(2-fluoroethoxymethyl)phenyl]methyl]-2-methyl-1,8-naphthyridine-3-carboxamide

HRID 929372
Notes
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Reaction equation

HRID 929372 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][NH:23][C:24]([C:26]3[C:27]([CH3:36])=[N:28][C:29]4[C:34]([CH:35]=3)=[CH:33][CH:32]=[CH:31][N:30]=4)=[O:25])=[CH:18][C:17]=2[F:37])(=O)=O)=CC=1.C1N2CCOCCOCCN(CCOCCOCC2)CCOCCOC1.[F-:64].[K+]>CC#N.O>[F:37][C:17]1[CH:18]=[C:19]([CH2:22][NH:23][C:24]([C:26]2[C:27]([CH3:36])=[N:28][C:29]3[C:34]([CH:35]=2)=[CH:33][CH:32]=[CH:31][N:30]=3)=[O:25])[CH:20]=[CH:21][C:16]=1[CH2:15][O:14][CH2:13][CH2:12][F:64]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 728012,2,2-CryptandHCID 522689Potassium FluorideHCID 896472142-[[2-Fluoro-4-[[(2-methyl-1,8-naphthyridine-3-carbonyl)amino]methyl]phenyl]methoxy]ethyl 4-methylbenzenesulfonate

Product 1

HCID 78122360N-[[3-fluoro-4-(2-fluoroethoxymethyl)phenyl]methyl]-2-methyl-1,8-naphthyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6342AcetonitrileSolvent

Procedure

A flask with a solution of 19 mg 2-[[2-fluoro-4-[[(2-methyl-1,8-naphthyridine-3-carbonyl)amino]methyl]phenyl]methoxy]ethyl 4-methylbenzenesulfonate (0.036 mmol), 26 mg Kryptofix 222 (4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]-hexacosane) (0.069 mmol) and 4 mg KF (0.069 mmol) in 1.0 ml dry MeCN was added to a preheated oil bath and heated at 90 C for 30 min. The reaction mixture was cooled to room temperature and diluted with water. The mixture was extracted twice with EtOAc. The combined organic phases were washed with brine, dried (MgSO4) and concentrated. Flash chromatography gave 9.6 mg (72%).

Workup

  1. temperatureheated at 90 C for 30 min
  2. extractionThe mixture was extracted twice with EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customFlash chromatography gave 9.6 mg (72%)

Sources & evidence

ORD record
ord-ed5f4861cf834ccaa64a34d401950b2e
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09295738B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes