Hydrochloric Acid → HCID 59850051, compound

HRID 333689Notes

Reaction equation

HRID 333689 reaction equation
[OH-].[NH4+:2].[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([C@H:14]([CH3:33])[C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=3)[CH2:19][CH2:18]1)=[O:16])[CH2:9][CH2:8][CH2:7]2.Cl>C(#N)C>[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([C@H:14]([CH3:33])[C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][C:26]([S:29]([NH2:2])(=[O:31])=[O:30])=[CH:25][CH:24]=3)[CH2:19][CH2:18]1)=[O:16])[CH2:9][CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 59850053HCID 59850053, compound

Product 1

HCID 59850051HCID 59850051, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Ammonium hydroxide (28-30% solution, 7.5 mL) was added dropwise to a solution of the (R)-4-(4-(2-(6-fluoro-3,4-dihydroquinolin-1(2H)-yl)propanoyl)piperazin-1-yl)benzene-1-sulfonyl chloride (375 mg, 0.56 mmol) in acetonitrile (5 mL) at 0° C. The reaction mixture was stirred at 0° C. for 4 h. The solution was cooled to 0° C. and aqueous 1.0 M HCl was added dropwise. The reaction mixture was extracted with CH2Cl2 (3×50 mL). The combined organic phases were dried over MgSO4. After evaporating the solvents under reduced pressure, the residue was purified by silica gel chromatography using 2-10% methanol in CH2Cl2 to give (R)-4-(4-(2-(6-fluoro-3,4-dihydroquinolin-1(2H)-yl)propanoyl)piperazin-1-yl)benzene sulfonamide as colourless oil (94 mg). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=447.1; tR=2.68 min.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. extractionThe reaction mixture was extracted with CH2Cl2 (3×50 mL)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customAfter evaporating the solvents under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b7961bb59cb34136b1ce6e0ff2ce383a
Source dataset
uspto-grants-2014_11
Patent number
US08883766B2

Reaction notes

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