Hydrochloric Acid → (S)-1-{5-Fluoro-6-[(S)-3-methylpiperazin-1-yl]pyridin-3-yl}ethane-1,2-diol

HRID 920135Notes

Reaction equation

HRID 920135 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([F:20])=[CH:18][C:17]([C@H:21]3[CH2:25][O:24]C(C)(C)[O:22]3)=[CH:16][N:15]=2)[CH2:10][C@@H:9]1[CH3:28])=O)(C)(C)C.Cl.C(OCC)C>C(Cl)Cl.CO.O1CCOCC1>[F:20][C:19]1[CH:18]=[C:17]([C@H:21]([OH:22])[CH2:25][OH:24])[CH:16]=[N:15][C:14]=1[N:11]1[CH2:12][CH2:13][NH:8][C@@H:9]([CH3:28])[CH2:10]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 71165120(S)-Tert-butyl-4-{5-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-fluoropyridin-2-yl}-2-methylpiperazine-1-carboxylate

Product 1

HCID 71145414(S)-1-{5-Fluoro-6-[(S)-3-methylpiperazin-1-yl]pyridin-3-yl}ethane-1,2-diolYield 113.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 116 (1.71 g, 4.33 mmol) in DCM (9.60 mL) and MeOH (1.50 mL) was added 4N HCl in dioxane (6.49 mL) to form a reaction mixture. The reaction mixture was stirred at a temperature of about 25° C. in a closed vessel for 16 h. Thereafter, the resulting suspension was stirred with diethyl ether. The solid precipitate was collected on filter paper and washed several times with diethyl ether to provide 1.25 g of 117 as a tan solid (88% yield) which, being >99% pure as analyzed by LC/MS, was used directly in the next step.

Workup

  1. customto form a reaction mixture
  2. customThe solid precipitate was collected
  3. filtrationon filter paper
  4. washwashed several times with diethyl ether

Sources & evidence

ORD record
ord-4a5b00fb62984005b178f325e3ebaa60
Source dataset
uspto-grants-2016_03
Patent number
US09273043B2

Reaction notes

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