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Dimethylformamide → 5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid ((S)-2-oxo-pyrrolidin-3-yl)-amide

HRID 2245265
Notes
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Reaction equation

HRID 2245265 reaction equation
N1C2C(=NC=CC=2)N([N:10]2[C:14](/[CH:15]=[C:16]3\[C:17](=[O:26])[NH:18][C:19]4[C:24]\3=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)=[C:13]([CH3:27])[C:12]([C:28]([O-:30])=O)=[C:11]2[CH3:31])N=1.[CH3:32][CH2:33][N:34](C(C)C)C(C)C.[CH3:41][N:42]([CH:44]=[O:45])C>>[O:45]=[C:44]1[C@@H:33]([NH:34][C:28]([C:12]2[C:13]([CH3:27])=[C:14](/[CH:15]=[C:16]3\[C:17](=[O:26])[NH:18][C:19]4[C:24]\3=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[NH:10][C:11]=2[CH3:31])=[O:30])[CH2:32][CH2:41][NH:42]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 131727992(Z)-3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylate

Product 1

HCID 592159295-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid ((S)-2-oxo-pyrrolidin-3-yl)-amideYield 27%

Procedure

To the solution of A4 (334 mg, 0.8 mmol) and DIEA (1 mL) in 20 mL of DMF was added 25b (120 mg, 1.28 mmol). The reaction mixture was stirred at room temperature for several hours. LC/MS was applied to determine completion of the reaction. DMF was evaporated under reduced pressure and the residue was precipitated with 5% diethylamine/methanol (10 mL). The precipitate was collected by filtration, washed with ethanol and dried in vacuum to give title compound as an orange solid (83 mg, 27% yield). 1H NMR (300 MHz, DMSO-d6): δ=13.68 (s, 1H), 10.89 (s, 1H), 7.71-7.82 (m, 4H), 6.82-6.96 (m, 2H), 4.47-4.56 (q, 1H), 3.18-3.25 (m, 2H), 2.42-2.45 (ds, 6H), 2.27-2.39 (m, 1H), 1.92-2.00 (q, 1H). LC/MS: 383.0 [M+H]+.

Workup

  1. customcompletion of the reaction
  2. customDMF was evaporated under reduced pressure
  3. customthe residue was precipitated with 5% diethylamine/methanol (10 mL)
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with ethanol
  6. customdried in vacuum

Sources & evidence

ORD record
ord-a5e239a232d64d4d922756a946bdd4bc
Source dataset
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07683057B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes