Ethanol → HCID 23627582, compound

HRID 1663262Notes

Reaction equation

HRID 1663262 reaction equation
C(C1C=CC(CC[CH:11]([CH:15]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]2[S:29]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=2)(=[O:31])=[O:30])[C:12]([NH2:14])=[O:13])=CC=1)#N.C(=O)([O-])[O-].[NH4+:44].[NH4+:45].[CH2:46](O)[CH3:47]>Cl>[C:23]([C:22]1[CH:21]=[CH:20][C:19]([CH2:46][CH2:47][NH:14][C:12](=[O:13])[CH2:11][CH:15]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]2[S:29]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=2)(=[O:30])=[O:31])=[CH:18][CH:17]=1)(=[NH:45])[NH2:44]

Participants

5

Reactant 3

HCID 702EthanolHCID 517111Ammonium CarbonateHCID 86635301HCID 86635301, compound

Product 1

HCID 23627582HCID 23627582, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-[2-(4-cyano-phenyl)-ethyl]-2-[5-(3,4-dichloro-benzenesulfonyl)-5,6-dihydro-phenanthridin-6-yl]-acetamide (Example 7) (200 mg, 0.35 mmol) in 9M hydrogen chloride in ethanol (10 mL) was allowed to stand overnight at room temperature, then the mixture was concentrated in vacuo. The residue was dissolved in ethanol (10 mL) and ammonium carbonate (335 mg, 3.5 mmol) was added. The reaction mixture was stirred overnight at room temperature then concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (dichloromethane:methanol:NH4OH=5:1:0.1) to yield 113 mg (55%) of the title compound as white crystals. MS (EI) 594.1 (MH+).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethanol (10 mL)
  3. concentrationthen concentrated in vacuo
  4. customThe residue was purified by preparative thin-layer chromatography (dichloromethane:methanol:NH4OH=5:1:0.1)

Sources & evidence

ORD record
ord-7a081a4170fd49858e752668debe463f
Source dataset
uspto-grants-2011_10
Patent number
US08034827B2

Reaction notes

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