HCID 53814372, compound → HCID 54204106, compound

HRID 1532341Notes

Reaction equation

HRID 1532341 reaction equation
[C:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([CH2:14][CH2:15][C@@H:16]3[CH2:20][CH2:19][CH2:18][N:17]3[CH:21]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:22]([O:24]CC)=[O:23])[N:10]2[CH3:13])=[CH:6][CH:5]=1)(=[NH:3])[NH2:2]>Cl>[C:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([CH2:14][CH2:15][C@@H:16]3[CH2:20][CH2:19][CH2:18][N:17]3[CH:21]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:22]([OH:24])=[O:23])[N:10]2[CH3:13])=[CH:6][CH:5]=1)(=[NH:2])[NH2:3]

Participants

3

Reactant 1

HCID 53814372HCID 53814372, compound

Product 1

HCID 54204106HCID 54204106, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

13 g of ethyl 2-[(S)-2-[2-(6-amidino-1-methylindol-2-yl)ethyl]-pyrrolidinyl]-2-phenylacetate obtained in Example 2 was dissolved in 5 ml of 35% hydrochloric acid solution, and the resulting solution was heated to 60° C. and stirred for 1.5 hours, and then stirred at room temperature overnight. The reaction solvent was removed by distillation under reduced pressure. The residue was purified with column chromatography [eluent: dichloromethane/methanol(2:3)] on NH-DM1020 silica. The fractions containing the desired product were combined and then distilled under reduced pressure to obtain 6.2 mg of the title compound as a pale yellow solid.

Workup

  1. stirringstirred at room temperature overnight
  2. customThe reaction solvent was removed by distillation under reduced pressure
  3. customThe residue was purified with column chromatography [eluent: dichloromethane/methanol(2:3)] on NH-DM1020 silica
  4. additionThe fractions containing the desired product
  5. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-e7ad8ab4270c4047b5de4bbd0252f839
Source dataset
uspto-grants-2001_03
Patent number
US06201006B1

Reaction notes

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