Hydrochloric Acid → HCID 178473990, compound

HRID 1269951Notes

Reaction equation

HRID 1269951 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].Cl.[CH3:13][N:14]([CH3:32])[C@H:15]1[CH2:20][CH2:19][C@H:18]([O:21][C:22]2[C:23]([CH3:31])=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][N:26]=[CH:25]3)[CH2:17][CH2:16]1>CN(C)C=O.O>[C:8]([N:27]1[C:28]2[C:24](=[C:23]([CH3:31])[C:22]([O:21][C@H:18]3[CH2:17][CH2:16][C@H:15]([N:14]([CH3:32])[CH3:13])[CH2:20][CH2:19]3)=[CH:30][CH:29]=2)[CH:25]=[N:26]1)(=[O:10])[CH3:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chloride2×HCID 8471Triethylamine2×HCID 178431639HCID 178431639, compound

Product 1

HCID 178473990HCID 178473990, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, triethylamine (112 μl, 0.807 mmol) and acetyl chloride (25.2 μl, 0.355 mmol) were added to a solution of monohydrochloride (100 mg, 0.323 mmol) of the trans-N,N-dimethyl-N-{4-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexyl}amine obtained in Example 412 in N,N-dimethylformamide (2 ml) at room temperature. After 1 hour, triethylamine (0.420 mmol) and acetyl chloride (0.355 mmol) were further added thereto. After 2 hours, the reaction solution was poured into water and extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol) to obtain trans-N-{4-[(1-acetyl-4-methyl-1H-indazol-5-yl)oxy]cyclohexyl}-N,N-dimethylamine (20.1 mg, 20%).

Workup

  1. waitAfter 2 hours
  2. extractionextracted with chloroform
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customThe organic layer dried
  5. concentrationwas concentrated under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-fe9eaeb43fae4e298de40d268513f928
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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