Ethyl 1-(aminomethyl)cyclohexane-1-carboxylate → 1-{[6-(2-Methylcarbamoyl-pyridin-4-yloxy)-benzooxazol-2-ylamino]methyl}-cyclohexanecarboxylic acid ethyl ester

HRID 1922202Notes

Reaction equation

HRID 1922202 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:12][NH2:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].CS([C:17]1[O:18][C:19]2[CH:25]=[C:24]([O:26][C:27]3[CH:32]=[CH:31][N:30]=[C:29]([C:33]([NH:35][CH3:36])=[O:34])[CH:28]=3)[CH:23]=[CH:22][C:20]=2[N:21]=1)=O>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1([CH2:12][NH:13][C:17]2[O:18][C:19]3[CH:25]=[C:24]([O:26][C:27]4[CH:32]=[CH:31][N:30]=[C:29]([C:33](=[O:34])[NH:35][CH3:36])[CH:28]=4)[CH:23]=[CH:22][C:20]=3[N:21]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 21840381Ethyl 1-(aminomethyl)cyclohexane-1-carboxylateHCID 57725414N-methyl-4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)picolinamide

Product 1

HCID 248210661-{[6-(2-Methylcarbamoyl-pyridin-4-yloxy)-benzooxazol-2-ylamino]methyl}-cyclohexanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-aminomethyl-cyclohexanecarboxylic acid ethyl ester in THF was added 4-(2-methanesulfinyl-benzooxazol-6-yloxy)-pyridine-2-carboxylic acid methylamide from Step 3 of Example 2. After reacting at room temperature for 2 hours the solvent was removed and the crude product was diluted with ethyl acetate and some dichloromethane, then washed three times with brine, dried with anhydrous sodium sulfate, filtered and concentrated. The final product was purified by reverse phase preparatory HPLC. MH+=453.1.

Workup

  1. customthe solvent was removed
  2. additionthe crude product was diluted with ethyl acetate
  3. washsome dichloromethane, then washed three times with brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe final product was purified by reverse phase preparatory HPLC

Sources & evidence

ORD record
ord-eb1caa711f904382a608f368408fa7cb
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

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