Hydrochloric Acid → HCID 68434681, compound

HRID 1297503Notes

Reaction equation

HRID 1297503 reaction equation
[OH-].[Li+].[NH2:3][C:4]1[N:9]=[C:8]([NH:10][CH2:11][CH2:12][CH2:13][N:14]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])[CH:16]=[C:15]2[C:27]([O:29]CC2C=CC=CC=2)=[O:28])[CH:7]=[CH:6][C:5]=1[N+:37]([O-:39])=[O:38].Cl>C1COCC1.O>[NH2:3][C:4]1[N:9]=[C:8]([NH:10][CH2:11][CH2:12][CH2:13][N:14]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])[CH:16]=[C:15]2[C:27]([OH:29])=[O:28])[CH:7]=[CH:6][C:5]=1[N+:37]([O-:39])=[O:38]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58914802HCID 58914802, compound

Product 1

HCID 68434681HCID 68434681, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Solid lithium hydroxide (20 eq) was added to a stirred solution of 1-{3-[(6-amino-5-nitro(2-pyridyl))amino]propyl}-4-(2,4-dichlorophenyl)pyrrole-2-carboxylate (10) (1 eq) in THF and water at rt. The mixture was heated to 50° C. for 12 h until complete by LC/MS. The reaction was allowed to cool to room temperature and acidified with 1 M HCl (aq.). The acidic solution was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered, and concentrated to pure 1-{3-[(6-amino-5-nitro(2-pyridyl))amino]propyl}-4-(2,4-dichlorophenyl)pyrrole-2-carboxylic acid (11) as a sticky yellow solid (99% yield).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe acidic solution was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-39872a76556e44479186abcb0b9ee023
Source dataset
uspto-grants-2007_07
Patent number
US07250443B2

Reaction notes

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