Hydrochloric Acid → HCID 58189143, compound

HRID 1423130Notes

Reaction equation

HRID 1423130 reaction equation
[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]3[C:15]=2[CH:16]=[CH:17][C:18]([C:26]([F:29])([F:28])[F:27])=[N:19]3)[CH2:11][CH2:10][N:9]1[CH2:30][C:31]([NH:33][O:34]C1CCCCO1)=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.Cl>CO.O1CCOCC1>[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]3[C:15]=2[CH:16]=[CH:17][C:18]([C:26]([F:28])([F:29])[F:27])=[N:19]3)[CH2:11][CH2:10][N:9]1[CH2:30][C:31]([NH:33][OH:34])=[O:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86651999HCID 86651999, compound

Product 1

HCID 58189143HCID 58189143, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

The intermediate 2-((S)-2-benzyl-4-(8-methoxy-2-(trifluoromethyl)quinolin-5-yl)piperazin-1-yl)-N-(tetrahydro-2H-pyran-2-yloxy)acetamide (130 mg, 0.23 mmol) was dissolved in MeOH (5 mL) and water (1 mL) and treated with a 4 N HCl solution in dioxane (250 mL). The resulting mixture was allowed to stir for 16 h after which time the reaction was evaporated to a small volume and partitioned between EtOAc (20 mL) and water (10 mL). The solution was adjusted to pH ˜7 with a saturated aqueous NaHCO3 solution and the organic portion further washed with brine (2×5 mL), dried over Na2SO4, filtered, and evaporated to afford the title compound as a yellow solid (108 mg, 97%). LC/MS (Method A) 5.16 min, [M+1]+ 475.

Workup

  1. customwas evaporated to a small volume
  2. custompartitioned between EtOAc (20 mL) and water (10 mL)
  3. washthe organic portion further washed with brine (2×5 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-f0eb544843404f78b62c7200ea72f676
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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