Hydrochloric Acid → HCID 58016729, compound

HRID 1517124Notes

Reaction equation

HRID 1517124 reaction equation
C(OC(N1CC[N:11]([C:14]([C:16]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)=[CH:20][C:19]([CH3:32])=[C:18]([C:33]([N:35]3[CH2:40][CH2:39][CH:38]([N:41]4[CH2:45][CH2:44][CH2:43][CH2:42]4)[CH2:37][CH2:36]3)=[O:34])[N:17]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CO.O1CCOCC1>[NH:11]1[CH2:14][CH2:9][CH:10]([NH:11][C:14]([C:16]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:30])([F:29])[F:31])[CH:23]=3)=[CH:20][C:19]([CH3:32])=[C:18]([C:33]([N:35]3[CH2:36][CH2:37][CH:38]([N:41]4[CH2:42][CH2:43][CH2:44][CH2:45]4)[CH2:39][CH2:40]3)=[O:34])[N:17]=2)=[O:15])[CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57441168HCID 57441168, compound

Product 1

HCID 58016729HCID 58016729, compoundYield 150.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.20 g (0.31 mmol) of 4-[5-methyl-6-(4-pyrrolidin-1-yl-piperidine-1-carbonyl)-3-(3-trifluoromethyl-phenyl)-pyridine-2-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (example 59) in 10 ml of MeOH was treated with 0.39 ml (1.56 mmol) of HCl in dioxane (4 molar) and the reaction mixture was then stirred at RT. After 18 hours, it was evaporated, poured into crashed ice, the pH was adjusted to 8-9 with sodium carbonate solution and the mixture was then extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 95:5 to 4:1) to give 0.127 g (75%) of the title compound as light yellow solid. MS: 544.3 (MH+).

Workup

  1. customit was evaporated
  2. additionpoured
  3. extractionthe mixture was then extracted twice with CH2Cl2
  4. washthe organic phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 95:5 to 4:1)

Sources & evidence

ORD record
ord-65ff82e53d4643c481882bb794e824ee
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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