Benzoic Acid → N-((1S,2R)-2-{[(cyanomethyl)amino]carbonyl}cyclohexyl)-4-[1-(2-methoxyethyl)piperidin-4-yl]benzamide

HRID 1593988Notes

Reaction equation

HRID 1593988 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]1[NH:13][C:14](=[O:20])OC(C)(C)C)=[O:6])#[N:2].C(O)(=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24]C=1.CCN=C=NCCCN(C)C.[CH:41]1[CH:42]=[CH:43][C:44]2N(O)N=N[C:45]=2[CH:46]=1.C[N:52]1C[CH2:56][O:55][CH2:54][CH2:53]1>CN(C=O)C>[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]1[NH:13][C:14](=[O:20])[C:41]1[CH:42]=[CH:43][C:44]([CH:26]2[CH2:25][CH2:24][N:52]([CH2:53][CH2:54][O:55][CH3:56])[CH2:22][CH2:27]2)=[CH:45][CH:46]=1)=[O:6])#[N:2]

Participants

7

Reactant 5

HCID 243Benzoic AcidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 60098559tert-butyl (1S,2R)-2-{[(cyanomethyl)amino]carbonyl}cyclohexylcarbamate

Product 1

HCID 11453077N-((1S,2R)-2-{[(cyanomethyl)amino]carbonyl}cyclohexyl)-4-[1-(2-methoxyethyl)piperidin-4-yl]benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 105 mg (0.58 mmol) of the amine from step 3 dissolved in 10 mL DMF was added 175 mg (0.58 mmol) of 1-(2-methoxyethyl)piperidin-4-yl]benzoic acid (this acid was prepared according to the procedure described in PCT Int. Appl. WO 01/58886), 110 mg (0.58 mmol) of EDCI, 78 mg (0.58 mmol) of HOBT and 0.22 mL (2.02 mmol) of N-methylmorpholine. The reaction mixture was stirred at room temperature overnight, partitioned between ethyl acetate and water, dried over magnesium sulfate and concentrated. Column chromatography, eluting with 10% methanol in dichloromethane provided 27.8 mg of the title compound N-((1S,2R)-2-{[(cyanomethyl)amino]carbonyl}cyclohexyl)-4-[1-(2-methoxyethyl)piperidin-4-yl]benzamide.

Workup

  1. customwas prepared
  2. custompartitioned between ethyl acetate and water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. washColumn chromatography, eluting with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-2e7d13e4394e4b4386fdfb58a39139c7
Source dataset
uspto-grants-2007_11
Patent number
US07300934B2

Reaction notes

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