Trifluoroacetic acid → HCID 59631180, compound

HRID 2360604Notes

Reaction equation

HRID 2360604 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:19]CC3C=CC(OC)=CC=3)=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>ClCCl>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH2:19])=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59631067HCID 59631067, compound

Product 1

HCID 59631180HCID 59631180, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 7-fluoro-N-(4-methoxybenzyl)-3-methyl-2-(pyridin-2-yl)quinolin-4-amine (0.486 g, 1.30 mmol) in dichloromethane (13.0 mL) was added TFA (0.5 mL, 6.49 mmol). Stirring continued at 23° C. for 26 hours. After which, the reaction was concentrated in vacuo, dissolved in ethyl acetate and washed with a saturated solution of sodium bicarbonate. The combined organic layers were concentrated in vacuo and purified on silica gel eluting with 0-10% methanol in dichloromethane to give the desired product 7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine. Mass Spectrum (ESI) m/e=254.1 (M+1).

Workup

  1. concentrationAfter which, the reaction was concentrated in vacuo
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with a saturated solution of sodium bicarbonate
  4. concentrationThe combined organic layers were concentrated in vacuo
  5. custompurified on silica gel eluting with 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-963f4c1918004cd1863aba17480dd47b
Source dataset
uspto-grants-2014_04
Patent number
US08686137B2

Reaction notes

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