Hydrochloric Acid → HCID 178422703, compound

HRID 1604607Notes

Reaction equation

HRID 1604607 reaction equation
[Cl:1][C:2]1[C:20]([N:21]([C:23](=[O:54])[CH2:24][NH:25][C:26](=[O:53])[CH:27]=[CH:28][C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36]([NH:45]C(OC(C)(C)C)=O)=[N:37]C(OC(C)(C)C)=O)=[CH:31][CH:30]=2)[CH3:22])=[CH:19][CH:18]=[C:17]([Cl:55])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2.Cl>C(OCC)(=O)C.CO>[Cl:1][C:2]1[C:20]([N:21]([C:23](=[O:54])[CH2:24][NH:25][C:26](=[O:53])[CH:27]=[CH:28][C:29]2[CH:30]=[CH:31][C:32]([NH:35][C:36]([NH2:45])=[NH:37])=[CH:33][CH:34]=2)[CH3:22])=[CH:19][CH:18]=[C:17]([Cl:55])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178422702HCID 178422702, compound

Product 1

HCID 178422703HCID 178422703, compoundYield 31.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-[2,6-dichloro-3-[N-[4-[2,3-bis(tert-butoxycarbonyl)guanidino]cinnamoylglycyl]-N-methylamino]benzyloxy]-2-methylquinoline (51 mg) in ethyl acetate and methanol was added 4N solution of hydrogen chloride in methanol (0.5 ml), and themixture was stirred for 2 days at ambient temperature. The mixture was concentrated in vacuo, and the residuewas dissolved in methaol. The solution was adjusted to pH 7 to 8 with aqueous ammonia and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform-methanol-aqueous ammonia) to give 8-[2,6-dichloro-3-[N-(4-guanidinocinnamoylglycyl)-N-methylamino]benzyloxy]-2-methylquinoline (12 mg) as amorphous powder.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residuewas dissolved in methaol
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative thin-layer chromatography (chloroform-methanol-aqueous ammonia)

Sources & evidence

ORD record
ord-3d7b675bde444362a70dc2aa6ef55dd5
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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