Hydrochloric Acid → 6-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-hexanoic acid

HRID 251664Notes

Reaction equation

HRID 251664 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]([C:12]1[C:16]([CH3:17])=[C:15]([CH:18]=[N:19][N:20]=[C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([F:30])[CH:28]=3)[NH:23][C:22]2=[O:31])[NH:14][C:13]=1[CH3:32])=[O:11].CO.[Li+].[OH-].Cl>O>[F:30][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22](=[O:31])[C:21]2=[N:20][N:19]=[CH:18][C:15]1[NH:14][C:13]([CH3:32])=[C:12]([C:10]([NH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:33])=[O:2])=[O:11])[C:16]=1[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 1363879506-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-hexanoic acid methyl ester

Product 1

HCID 1363879516-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-hexanoic acidYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-hexanoic acid methyl ester (455 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 (163 mg, 37% yield) as a red solid. LC-MS (m/z) 442 (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-70fe90fb276a4219bfc1a213ee6567ee
Source dataset
uspto-grants-2011_01
Patent number
US07863315B2

Reaction notes

Loading…