Carbamic acid,N-[2-[(R)-(3-chlorophenyl)(3R)-3-piperidinylmethoxy]ethyl]-,methyl ester → HCID 178502137, compound

HRID 451900Notes

Reaction equation

HRID 451900 reaction equation
[C:1]([N:3]=[C:4]([NH:7][C@@H:8]([CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])SC)#[N:2].[Cl:26][C:27]1[CH:28]=[C:29]([C@@H:33]([C@@H:42]2[CH2:47][CH2:46][CH2:45][NH:44][CH2:43]2)[O:34][CH2:35][CH2:36][NH:37][C:38](=[O:41])[O:39][CH3:40])[CH:30]=[CH:31][CH:32]=1>CN(C=O)C.CCN(CC)CC.C(OCC)(=O)C>[Cl:26][C:27]1[CH:28]=[C:29]([C@@H:33]([C@@H:42]2[CH2:47][CH2:46][CH2:45][N:44]([C:4](=[N:3][C:1]#[N:2])[NH:7][C@H:8]([CH2:9][N:10]([CH3:18])[C:11]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:17])[CH2:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH2:43]2)[O:34][CH2:35][CH2:36][NH:37][C:38](=[O:41])[O:39][CH3:40])[CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 2

HCID 59598478Carbamic acid,N-[2-[(R)-(3-chlorophenyl)(3R)-3-piperidinylmethoxy]ethyl]-,methyl esterHCID 178503934HCID 178503934, compound

Product 1

HCID 178502137HCID 178502137, compoundYield 2.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of (S)-tert-butyl 2-((cyanoimino)(methylthio)methylamino)-3-cyclohexylpropyl(methyl)carbamate (200 mg, 0.543 mmol) in DMF (8 mL) and Et3N (0.5 mL) was added methyl 2-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)ethylcarbamate (178 mg, 0.543 mmol). The mixture was heated at 100-110° C. for 48 h. The reaction mixture was diluted with ethyl acetate (100 mL), washed with water (30 mL×4), dried over Na2SO4 and concentrated to give the residue, which was purified by column to give methyl 2-((R)-(3-chlorophenyl)((R)-1-(N′-cyano-N—((S)-1-cyclohexyl-3-(N-methyl-N-(tert-butoxycarbonyl)amino)propan-2-yl)carbamimidoyl)piperidin-3-yl)methoxy)ethylcarbamate (8 mg, 2%).

Workup

  1. washwashed with water (30 mL×4)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give the residue, which
  5. customwas purified by column

Sources & evidence

ORD record
ord-90b772a167e844f588838d8d1993242f
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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