Diisopropylethylamine → HCID 178473534, compound

HRID 25241Notes

Reaction equation

HRID 25241 reaction equation
[I-].ClC1C=CC=C[N+]=1C.[CH2:10]([O:12][C:13](=[O:23])[NH:14][C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=S)[CH3:11].Cl.Cl.[NH2:26][CH:27]([CH2:40][CH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1)[C:28]([NH:30][C:31]1([C:38]#[N:39])[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]1)=[O:29].C(N(CC)C(C)C)(C)C>ClCCl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH2:10]([O:12][C:13](=[O:23])[N:14]=[C:15]([NH:26][CH:27]([C:28](=[O:29])[NH:30][C:31]1([C:38]#[N:39])[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]1)[CH2:40][CH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1)[N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[CH3:11]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 2824559Ethyl (morpholin-4-ylcarbonothioyl)carbamateHCID 225663392-amino-N-(-4-cyano-1-methyl-piperidin-4-yl)-3-cyclohexylpropionamide bis hydrochloride salt

Product 1

HCID 178473534HCID 178473534, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

2-Chloro-N-methylpyridinium iodide (680 mg, 2.66 mmol), was added to a solution of (morpholine-4-carbothioyl)-carbamic acid ethyl ester (450 mg, 2.06 mmol), 2-amino-N-(4-cyano-1-methyl-piperidin-4-yl)-3-cyclohexyl-propionamide bis hydrochloride salt (745 mg, 2.04 mmol), and N,N-diisopropylethylamine (1.10 mL, 6.3 mmol) in dichloromethane (8.0 mL). The reaction was stirred at room temperature for 2.5 h then taken up in 10% citric acid solution and washed with EtOAc. The aqueous phase was then basified with saturated sodium carbonate and extracted with EtOAc. The organic extract was dried (MgSO4) and concentrated to provide the desired product as a white solid (250 mg, 26%). This material was further purified by HPLC using a 20×250 mm C18 reverse phase column with the method being 20% acetonitrile in water to 90% acetonitrile in water. MS, m/z 477=M+1.

Workup

  1. washwashed with EtOAc
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9b2ff7f0a0c44c8fbe2f7f2192754cef
Source dataset
uspto-grants-2005_02
Patent number
US06858623B2

Reaction notes

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