Hydrochloric Acid → HCID 178501940, compound

HRID 1269952Notes

Reaction equation

HRID 1269952 reaction equation
C(N(CC)CC)C.Cl[C:9]([O:11][CH3:12])=[O:10].Cl.[CH3:14][N:15]([CH3:33])[C@H:16]1[CH2:21][CH2:20][C@H:19]([O:22][C:23]2[C:24]([CH3:32])=[C:25]3[C:29](=[CH:30][CH:31]=2)[NH:28][N:27]=[CH:26]3)[CH2:18][CH2:17]1.[Cl-].[Na+]>CC(C)=O.C(Cl)(Cl)Cl>[CH3:14][N:15]([CH3:33])[C@H:16]1[CH2:17][CH2:18][C@H:19]([O:22][C:23]2[C:24]([CH3:32])=[C:25]3[C:29](=[CH:30][CH:31]=2)[N:28]([C:9]([O:11][CH3:12])=[O:10])[N:27]=[CH:26]3)[CH2:20][CH2:21]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 6586Methyl chloroformate2×HCID 8471Triethylamine2×HCID 178431639HCID 178431639, compound

Product 1

HCID 178501940HCID 178501940, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

Under a nitrogen atmosphere, triethylamine (135 μl, 0.968 mmol) and methyl chloroformate (37 μl, 0.484 mmol) were added at 0° C. 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 acetone (2 ml). After 15 minutes, the mixture thus obtained was warmed up to room temperature. After 1 hour, triethylamine (0.646 mmol) and methyl chloroformate (0.484 mmol) were further added thereto. After 1 hour, chloroform (2 ml) was added thereto. After another 3 hours, the reaction solution was poured into a saturated aqueous sodium chloride solution 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 methyl trans-5-{[4-(dimethylamino)cyclohexyl]oxy}-4-methyl-1H-indazole-1-carboxylate (38.7 mg, 36%).

Workup

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

Sources & evidence

ORD record
ord-f384863b0b614dc68a0121517448937f
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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