Hydrochloric Acid → HCID 178465975, compound

HRID 1081498

Reaction equation

HRID 1081498 reaction equation
[C:1]12([N:11]3[C:15]4[CH:16]=[C:17]([O:20][CH2:21][CH3:22])[CH:18]=[CH:19][C:14]=4[N:13]([S:23]([C:26]4[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][C:27]=4[O:33][CH3:34])(=[O:25])=[O:24])[C:12]3=[O:35])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:36]([N:38]([CH2:41][CH3:42])[C:39]#[N:40])[CH3:37].CCOC(C)=O.[ClH:49]>CCO>[OH2:20].[ClH:49].[C:1]12([N:11]3[C:15]4[CH:16]=[C:17]([O:20][CH2:21][CH3:22])[CH:18]=[CH:19][C:14]=4[N:13]([S:23]([C:26]4[CH:31]=[CH:30][C:29]([NH:32][C:39]([N:38]([CH2:41][CH3:42])[CH2:36][CH3:37])=[NH:40])=[CH:28][C:27]=4[O:33][CH3:34])(=[O:24])=[O:25])[C:12]3=[O:35])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

6

Reactant 4

HCID 313Hydrochloric Acid3×HCID 8857Ethyl AcetateHCID 12050Diethylcyanamide2×HCID 23364275HCID 23364275, compound

Product 1

HCID 178465975HCID 178465975, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A mixture of 1.5 g of the compound obtained in EXAMPLE 40 step B), 1.5 g of N,N-diethylcyanamide, 20 ml of AcOEt and 3 ml of a 20% solution of HCl in EtOH is refluxed for 22 hours. 2 g of N,N-diethylcyanamide and 3 ml of a 20% solution of HCl in EtOH are then added and reflux is continued for 5 hours. After cooling, the reaction mixture is extracted with AcOEt, the organic phase is washed with water, with a 1N solution of NaHCO3 and with water and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a DCM/AcOEt mixture (94/6; v/v) as the eluent. The product obtained is dissolved in EtOH, 1 ml of concentrated HCl is added and the mixture is evaporated under vacuum to give 0.2 g of the hydrochloride of the expected product after crystallization from an EtOH/ether mixture (50/50; v/v). M.p.=186° C.

Workup

  1. temperatureis refluxed for 22 hours
  2. temperaturereflux
  3. temperatureAfter cooling
  4. extractionthe reaction mixture is extracted with AcOEt
  5. washthe organic phase is washed with water, with a 1N solution of NaHCO3 and with water
  6. dry with materialdried over Na2SO4
  7. customthe solvent is evaporated off under vacuum
  8. customThe residue is chromatographed on silica using a DCM/AcOEt mixture (94/6; v/v) as the eluent
  9. customThe product obtained
  10. customthe mixture is evaporated under vacuum

Sources & evidence

ORD record
ord-86b211b04b374aaeafe2b1d3e51278e3
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Linked notes

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