Hydrochloric Acid → HCID 67126486, compound

HRID 1848936Notes

Reaction equation

HRID 1848936 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]1([F:16])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[CH3:21][N:22]([CH3:27])[CH2:23][C:24](Cl)=[O:25].Cl.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]1([F:16])[CH2:15][CH2:14][N:13]([C:24](=[O:25])[CH2:23][N:22]([CH3:27])[CH3:21])[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 10340Sodium Carbonate2×HCID 70103442-(Dimethylamino)acetyl chloride2×HCID 67227863HCID 67227863, compound

Product 1

HCID 67126486HCID 67126486, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-chloro-6-((4-fluoropiperidin-4-yl)methoxy)pyridine-3-sulfonamide, 2•trifluoroacetic acid (0.131 g), 2-(dimethylamino)acetyl chloride, hydrochloric acid (0.139 g), and sodium carbonate (0.048 g) were combined in a 5-mL vial with N,N-dimethylformamide (3 mL) and stirred overnight at room temperature. Additional sodium carbonate (0.048 g) was added followed by 2-(dimethylamino)acetyl chloride, hydrochloric acid (0.139 g) and stirring was continued over a second night. The reaction mixture was concentrated under high vacuum, slurried in CH2Cl2, filtered, concentrated, chromatographed on amine functionalized silica gel with 0 to 4% methanol in CH2Cl2 as the eluent and dried in a vacuum oven at 80° C.

Workup

  1. stirringstirring
  2. waitwas continued over a second night
  3. concentrationThe reaction mixture was concentrated under high vacuum
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed on amine functionalized silica gel with 0 to 4% methanol in CH2Cl2 as the eluent
  7. customdried in a vacuum oven at 80° C.

Sources & evidence

ORD record
ord-21d5aca6cc194e75b4614f705532e928
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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