Hydrochloride methanol → Hydrochloric Acid

HRID 1678711Notes

Reaction equation

HRID 1678711 reaction equation
C(OC([N:8]([CH2:31][CH:32]([C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([N:47](C(OC(C)(C)C)=O)[S:48]([CH3:51])(=[O:50])=[O:49])[CH:42]=1)[O:33][Si](CC)(CC)CC)[CH2:9][CH2:10][O:11][C:12]1[CH:20]=[C:19]2[C:15]([C:16]([C:27]([F:30])([F:29])[F:28])=[N:17][N:18]2[C@H]2CCCCO2)=[CH:14][CH:13]=1)=O)(C)(C)C.[ClH:59].CO>>[OH:33][C@H:32]([C:41]1[CH:42]=[C:43]([NH:47][S:48]([CH3:51])(=[O:49])=[O:50])[CH:44]=[CH:45][CH:46]=1)[CH2:31][NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:20]=[C:19]2[C:15]([C:16]([C:27]([F:30])([F:29])[F:28])=[N:17][NH:18]2)=[CH:14][CH:13]=1.[ClH:59]

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 131729133HCID 131729133, compound

Product 2

HCID 313Hydrochloric AcidHCID 178505017HCID 178505017, compound

Conditions

Temperature
50 °C

Procedure

[Method 1] (R)-6-(2-(tert-butoxycarbonyl(2-(3-(N-(tert -butoxycarbonyl)methylsulfonamido)phenyl)-2-(triethylsilyloxy)ethyl)amino)ethoxy)-1-(tetrahydro -2H -pyran-2-yl)-3-trifluoromethylindazole (85.6 mg) that can be produced by the method described in Reference Example 30 or the like, was dissolved in a 10% hydrogen chloride-methanol solution (1.5 mL; manufactured by Tokyo Chemical Industry Co., Ltd.), and the solution was purged with nitrogen and stirred for 39 hours at 50° C. The reaction solution was cooled to room temperature, and then nitrogen gas was blown into the reaction solution to evaporate the solvent. The operation of adding diethyl ether to the residue, and blowing nitrogen gas into the reaction solution to evaporate the solvent, was repeated three times. The resulting residue was purified by HPLC, and then the purified product was dissolved in methanol (2 mL). A 10% hydrogen chloride-methanol solution (0.2 mL; manufactured by Tokyo Chemical Industry Co., Ltd.) was added to the solution, and nitrogen gas was blown into the solution to evaporate the solvent. The residue was dissolved in water (1 mL), and the solution was freeze-dried. Thus, the title compound was obtained in the form of hydrochloride (31 mg).

Workup

  1. customthe solution was purged with nitrogen
  2. temperatureThe reaction solution was cooled to room temperature
  3. customto evaporate the solvent
  4. customto evaporate the solvent
  5. customThe resulting residue was purified by HPLC
  6. dissolutionthe purified product was dissolved in methanol (2 mL)
  7. additionA 10% hydrogen chloride-methanol solution (0.2 mL; manufactured by Tokyo Chemical Industry Co., Ltd.) was added to the solution, and nitrogen gas
  8. customto evaporate the solvent
  9. dissolutionThe residue was dissolved in water (1 mL)
  10. customthe solution was freeze-dried

Sources & evidence

ORD record
ord-c9723f4aa729479f8fa7fed4c3baf506
Source dataset
uspto-grants-2011_08
Patent number
US08008506B2

Reaction notes

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