Hydrochloric Acid → 2-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-acetic acid

HRID 251656Notes

Reaction equation

HRID 251656 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][NH:5][C:6]([C:8]1[C:12]([CH3:13])=[C:11]([CH:14]=[N:15][N:16]=[C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([F:26])[CH:24]=3)[NH:19][C:18]2=[O:27])[NH:10][C:9]=1[CH3:28])=[O:7].CO.[Li+].[OH-].Cl>O>[F:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:27])[C:17]2=[N:16][N:15]=[CH:14][C:11]1[NH:10][C:9]([CH3:28])=[C:8]([C:6]([NH:5][CH2:4][C:3]([OH:29])=[O:2])=[O:7])[C:12]=1[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 1363879412-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-acetic acid methyl ester

Product 1

HCID 1363879432-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-acetic acidYield 33.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-acetic acid methyl ester (399 mg, 1 mmol) and 300 ml of CH3OH were stirred at room temperature while 25 ml of 4 N solution of LiOH in H2O was added. The mixture was stirred for 24 hours at room temperature. The mixture is neutralized with concentrated hydrochloric acid to pH 7 and evaporated under vacuum to remove methanol. The residue was adjusted to pH 3 with concentrated hydrochloric acid. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (128 mg, 33% yield) as a red solid. LC-MS (m/z) 386 (M+1).

Workup

  1. additionwas added
  2. customevaporated under vacuum
  3. customto remove methanol
  4. filtrationThe solids were collected by vacuum filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-24f047bd42b9426bb9b6b0709d31dfa2
Source dataset
uspto-grants-2011_01
Patent number
US07863315B2

Reaction notes

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