Hydrochloric Acid → HCID 66921189, compound

HRID 1949088Notes

Reaction equation

HRID 1949088 reaction equation
[F:1][C:2]([F:31])([F:30])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2([NH2:29])[CH2:18][CH2:17][N:16]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH2:15][CH2:14]2)=[O:12])=[CH:6][CH:5]=1.Cl.CI.[C:35](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:31][C:2]([F:1])([F:30])[O:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([C:13]2([NH:29][CH3:35])[CH2:18][CH2:17][N:16]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH2:15][CH2:14]2)=[O:12])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58129332HCID 58129332, compound

Product 1

HCID 66921189HCID 66921189, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 42 mg (0.08 mmol) 4-Amino-1-(toluene-4-sulfonyl)-piperidine-4-carboxylic acid (4-trifluoromethoxy-phenyl)-amide; hydrochloride (example 80) and 96 mg (0.68 mmol) methyl iodide and 17.6 mg (0.128 mmol) potassium carbonate in 2 mL DMF was heated to 40° C. for 1.5 h. The mixture was filtered and the filtrate was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3 to yield after evaporation of the product containing fractions 9.6 mg (24%) of the title compound. MS (m/e): 472.3 [(M+H)+].

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was subjected to purification by preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and NEt3
  5. customto yield
  6. customafter evaporation of the product
  7. additioncontaining fractions 9.6 mg (24%) of the title compound

Sources & evidence

ORD record
ord-5843a87719c742158b927e414dc17c36
Source dataset
uspto-grants-2013_03
Patent number
US08399676B2

Reaction notes

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