Dichloromethane → HCID 69144794, compound

HRID 2223919Notes

Reaction equation

HRID 2223919 reaction equation
N[CH2:2][CH2:3][C:4]1([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([N:18]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][N:27]=3)[C:19]([C:21]3[O:22][CH:23]=[CH:24][CH:25]=3)=[O:20])[CH2:14][CH2:13]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[C:33]([O:37][C:38]([NH:40][C:41](=[N:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])SC)=[O:39])([CH3:36])([CH3:35])[CH3:34].C([N:55](CC)C(C)C)(C)C.ClCCl>CN(C)C=O.[Hg](Cl)Cl>[C:33]([O:37][C:38]([N:40]([CH2:2][CH2:3][C:4]1([CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([N:18]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][N:27]=3)[C:19]([C:21]3[O:22][CH:23]=[CH:24][CH:25]=3)=[O:20])[CH2:16][CH2:17]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[C:41]([NH2:55])=[N:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[O:39])([CH3:36])([CH3:35])[CH3:34]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 5466031,3-DI-Boc-2-methylisothioureaHCID 59714922HCID 59714922, compound

Product 1

HCID 69144794HCID 69144794, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[1-[2-[1-(2-aminoethyl)cyclohexyl]ethyl]piperidin-4-yl]-N-(5-methylpyridin-2-yl)-2-furancarboxamide (synthesized in Example 3F-5) (104 mg) and 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (85 mg) in N,N-dimethylformamide (5 mL) were added N,N-diisopropylethylamine (0.12 g) and then mercury (II) chloride (113 mg) at room temperature. The solution was stirred at room temperature for 3 days. Dichloromethane was added to the solution and insolubles were filtered off with Celite. The solvent was distilled off under reduced pressure. The resulting residue was purified by chromatography [silica gel, dichloromethane-methanol-aqueous ammonia (97:3:0.2)] to give the title compound (0.1049 g).

Workup

  1. customat room temperature
  2. filtrationwere filtered off with Celite
  3. distillationThe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by chromatography [silica gel, dichloromethane-methanol-aqueous ammonia (97:3:0.2)]

Sources & evidence

ORD record
ord-96ae96923ad34ada8ba48c9e421bf553
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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