Hydrochloric Acid → HCID 178512396, compound

HRID 408643Notes

Reaction equation

HRID 408643 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][N:5]1[CH2:10][CH2:9][C:8]([CH2:19][NH:20][C:21]([NH2:34])=[N:22][C:23]([C:25]2[C:30]([NH2:31])=[N:29][C:28]([NH2:32])=[C:27]([Cl:33])[N:26]=2)=[O:24])([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][CH2:6]1.Cl>CO.[OH-].[Na+]>[NH2:31][C:30]1[C:25]([C:23]([N:22]=[C:21]([NH2:34])[NH:20][CH2:19][C:8]2([CH2:11][CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:7][CH2:6][N:5]([CH2:4][C:3]([OH:35])=[O:2])[CH2:10][CH2:9]2)=[O:24])=[N:26][C:27]([Cl:33])=[C:28]([NH2:32])[N:29]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178501521HCID 178501521, compound

Product 1

HCID 178512396HCID 178512396, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 145 mg (0.23 mmol) {4-[N′-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-guanidinomethyl]-4-phenethyl-piperidin-1-yl}-acetic acid methyl ester (Example 1.16) in 5 ml methanol and 235 μl 4 N NaOH is stirred at 50° C. for 1 hour. Then the solution is acidified with 470 μl 4 N HCl and concentrated under reduced pressure. The residue is purified by preparative reverse phase HPLC (gradient of acetonitrile and water+0.2% trifluoroacetic acid, 25° C.). Fractions containing the title compound were concentrated under reduced pressure.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is purified by preparative reverse phase HPLC (gradient of acetonitrile and water+0.2% trifluoroacetic acid, 25° C.)
  3. additionFractions containing the title compound
  4. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-24daad061e1340f8b818dbc6845d8c29
Source dataset
uspto-grants-2014_06
Patent number
US08759349B2

Reaction notes

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