Sodium Bicarbonate → HCID 68509815, compound

HRID 1716562Notes

Reaction equation

HRID 1716562 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=2[NH2:20])[CH:8]([O:21][CH3:22])[CH2:7]1)=[O:5])[CH3:2].C([O-])(O)=O.[Na+]>C(O)(=O)C(C)C.C(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([N:12]2[C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=3[N:20]=[C:15]2[CH:16]([CH3:19])[CH3:17])[CH:8]([O:21][CH3:22])[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 68509287HCID 68509287, compound

Product 1

HCID 68509815HCID 68509815, compoundYield 106%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6590Isobutyric AcidSolvent

Procedure

A solution of 4-(2-amino-4-methyl-phenylamino)-3-methoxy-piperidine-1-carboxylic acid ethyl ester (750 mg, 2.44 mmol) in isobutyric acid (15 mL) was subjected to microwave irradiation for 1 h with a resulting temperature of 180° C. The reaction mixture was cooled to rt and then diluted with CH2Cl2 (150 mL) and a saturated NaHCO3 solution (200 mL). The aqueous layer was extracted twice with CH2Cl2. The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (15/1 CH2Cl2/CH3OH) to yield 4-(2-isopropyl-5-methyl-benzoimidazol-1-yl)-3-methoxy-piperidine-1-carboxylic acid ethyl ester (465 mg, 56%) as a waxy solid.

Workup

  1. customirradiation for 1 h with a resulting temperature of 180° C
  2. extractionThe aqueous layer was extracted twice with CH2Cl2
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (15/1 CH2Cl2/CH3OH)

Sources & evidence

ORD record
ord-092428dea190472aaaf439bf5f03d5c1
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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