HCID 69109610, compound → HCID 69311708, compound

HRID 2220500Notes

Reaction equation

HRID 2220500 reaction equation
C(O[C:6]([N:8]1[CH:17]([C:18](=[O:34])[NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]3=[O:32])=[CH:22][C:21]=2[F:33])[CH2:16]C2N=CC=CC=2C1)=O)(C)(C)C>ClCCl.C(O)(C(F)(F)F)=O>[F:33][C:21]1[CH:22]=[C:23]([N:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]2=[O:32])[CH:24]=[CH:25][C:20]=1[NH:19][C:18]([CH:17]1[NH:8][CH2:6][C:31]2[N:26]=[CH:27][CH:28]=[CH:29][C:30]=2[CH2:16]1)=[O:34]

Participants

4

Reactant 1

HCID 69109610HCID 69109610, compound

Product 1

HCID 69311708HCID 69311708, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-7,8-dihydro-5H-[1,6]naphthyridine-6-carboxylic acid tert-butyl ester (310 mg) in 8 ml dichloromethane and 1.53 ml TFA was stirred for 4 hrs at rt. The reaction mixture was poured onto 1M NaOH/ice and extracted twice with dichloromethane. The organic layers were dried over magnesium sulfate, evaporated and purified by chromatography (silica gel, AcOEt/methanol 9:1) to deliver the title compound as a light yellow solid (151 mg). MS: 365.5 (M+H)+

Workup

  1. extractionextracted twice with dichloromethane
  2. dry with materialThe organic layers were dried over magnesium sulfate
  3. customevaporated
  4. custompurified by chromatography (silica gel, AcOEt/methanol 9:1)

Sources & evidence

ORD record
ord-5cc5c62e4dcb4933abf653f4b432ca42
Source dataset
uspto-grants-2008_08
Patent number
US07417144B2

Reaction notes

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