Trifluoroacetic acid → HCID 178426944, compound

HRID 2352925Notes

Reaction equation

HRID 2352925 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH:16]=[C:17]2[C:25]3[C:20](=[CH:21][C:22]([C:26](=[O:43])[C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([NH:33][C:34]([C:36]5[N:37]([CH3:42])[N:38]=[C:39]([CH3:41])[CH:40]=5)=[O:35])[CH:28]=4)=[CH:23][CH:24]=3)[NH:19][C:18]2=[O:44])=[CH:11][CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][CH:16]=[C:17]2[C:25]3[C:20](=[CH:21][C:22]([C:26]([C:27]4[CH:28]=[C:29]([NH:33][C:34]([C:36]5[N:37]([CH3:42])[N:38]=[C:39]([CH3:41])[CH:40]=5)=[O:35])[CH:30]=[CH:31][CH:32]=4)=[O:43])=[CH:23][CH:24]=3)[NH:19][C:18]2=[O:44])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178426946HCID 178426946, compound

Product 1

HCID 178426944HCID 178426944, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A dry 100 mL round bottom flask equipped with an Ar(g) inlet was charged with {4-[(6-{3-[(2,5-Dimethyl-2H-pyrazole-3-carbonyl)-amino]-benzoyl}-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-amino]-benzyl}-carbamic acid tert-butyl ester (as prepared in Example 203, 0.113 g, 0.186 mmol) and CH2Cl2 (0.622 mL). The resulting solution was cooled to 0° C. in an ice bath. TFA (0.015 mL) was then added and the reaction mixture was allowed to stir at 0° C. for 30 minutes after which the bath was removed and the reaction was allowed to stir at room temperature for an additional 1 h. Subsequently the reaction mixture was neutralized with saturated NaHCO3(aq) and then washed with EtOAc (3×20 mL). The combined organic layer was then dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude residue was chromatographed over silica (5% MeOH/95% CHCl3) to afford pure 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid (3-{3-[(4-aminomethyl-phenylamino)-methylene]-2-oxo-2,3-dihydro-1H-indole-6-carbonyl}-phenyl)-amide in 61% yield (0.057 g, 0.113 mmol).

Workup

  1. customwas removed
  2. stirringto stir at room temperature for an additional 1 h
  3. washwashed with EtOAc (3×20 mL)
  4. dry with materialThe combined organic layer was then dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was chromatographed over silica (5% MeOH/95% CHCl3)

Sources & evidence

ORD record
ord-962fafcb9d9e4c489af815771f79dcdf
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

Loading…