Hydrochloric Acid → HCID 86592482, compound

HRID 2099154Notes

Reaction equation

HRID 2099154 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:15][C:16]([C:18]2[N:19]=[N:20][N:21]([C:23]3[CH:28]=[C:27]([C:29](=[O:48])[NH:30][C:31]4[CH:36]=[C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:34]=[C:33]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])[C:32]=4[O:46][CH3:47])[CH:26]=[CH:25][C:24]=3[CH3:49])[CH:22]=2)=[O:17])[CH2:9]1)=O)(C)(C)C.Cl>C(Cl)Cl.O1CCOCC1.CO>[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][NH:15][C:16]([C:18]2[N:19]=[N:20][N:21]([C:23]3[CH:28]=[C:27]([C:29](=[O:48])[NH:30][C:31]4[CH:36]=[C:35]([C:37]([CH3:38])([CH3:39])[CH3:40])[CH:34]=[C:33]([NH:41][S:42]([CH3:45])(=[O:43])=[O:44])[C:32]=4[O:46][CH3:47])[CH:26]=[CH:25][C:24]=3[CH3:49])[CH:22]=2)=[O:17])[CH2:9]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 11765275HCID 11765275, compound

Product 1

HCID 86592482HCID 86592482, compoundYield 66.1%

Reagents, catalysts & solvents 3

HCID 887MethanolCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 336 mg (0.481 mmol) of 3-[({1-[5-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-2-methyl-phenyl]-1H-[1,2,3]triazole-4-carbonyl}-amino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (Example 72) in 5 mL CH2Cl2 was added dropwise 1.2 mL of 4N HCl in dioxane. As a gummy yellow precipitate began to form in the flask, 10 drops of MeOH were added and the solution was stirred overnight. The mixture was partitioned between CH2Cl2 (75 mL) and 50% saturated aqueous NaHCO3 (50 mL). The layers were separated and the aqueous portion was extracted with CH2Cl2 (2×30 mL). The combined extracts were washed with water (30 mL), brine (30 mL), dried (Na2SO4), filtered and concentrated to afford 190 mg of 1-[5-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-2-methyl-phenyl]-1H-[1,2,3]triazole-4-carboxylic acid (piperidin-3-ylmethyl)-amide as a pale yellow solid.

Workup

  1. additionwere added
  2. customThe mixture was partitioned between CH2Cl2 (75 mL) and 50% saturated aqueous NaHCO3 (50 mL)
  3. customThe layers were separated
  4. extractionthe aqueous portion was extracted with CH2Cl2 (2×30 mL)
  5. washThe combined extracts were washed with water (30 mL), brine (30 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-22b998264d9a4b278fceb91c6c7a0159
Source dataset
uspto-grants-2009_08
Patent number
US07569568B2

Reaction notes

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