Hydrochloric Acid → HCID 86647256, compound

HRID 1962884Notes

Reaction equation

HRID 1962884 reaction equation
C([O:3][C:4](=[O:27])[CH:5]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[C:17]([CH3:20])[C:18]=1[F:19])[N:15]=[CH:14][C:13]([C:21]#[C:22][Si](C)(C)C)=[CH:12]2)[S:6][CH3:7])C.[OH-].[Na+].Cl>C1COCC1>[C:21]([C:13]1[CH:14]=[N:15][C:16]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:8][CH:5]([S:6][CH3:7])[C:4]([OH:27])=[O:3])=[C:18]([F:19])[C:17]=2[CH3:20])#[CH:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66751658HCID 66751658, compound

Product 1

HCID 86647256HCID 86647256, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of (7-fluoro-8-methyl-3-trimethylsilanylethynyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid ethyl ester (3.35 g, 90% purity) from Step 7 in THF (100 ml), a 0.5 M aq NaOH soln (19.5 ml) was slowly added at 0° C. The light yellow mixture was stirred during 2 hrs at 0-10° C., then 2M HCl soln was added (pH 1). The mixture was extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over sodium sulphate anhydrous, filtered and concentrated under reduced pressure yielding (3-ethynyl-7-fluoro-8-methyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid which was used as such for the next step. 1H NMR (DMSO-d6) δ ppm: 13.60 (1H, br s); 8.85 (1H, d); 8.40 (1H, d); 7.560 (1H, d); 6.11 (1H, s); 4.50 (1H, s); 2.59 (3H, d); 2.17 (3H, s).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulphate anhydrous
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6cd2f256b7dc436eb073a823b21480a0
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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