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N,N'-Dimethylethylenediamine → HCID 86761624, compound

HRID 2389392
Notes
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Reaction equation

HRID 2389392 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14](C2N=CC=CN=2)[C:13](=O)[CH:12]3C)[CH:5]=[CH:6][C:7]=1[F:8].[C:26]([N:45]1C=NC(I)=N1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:51](=[O:54])([O-])[O-].[K+].[K+].CN[CH2:59][CH2:60][NH:61][CH3:62]>[Cu]I.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH3:10])[C:17]3[C:13](=[CH:12][CH:11]=[CH:15][CH:16]=3)[N:14]([C:62]3[N:61]=[CH:60][CH:59]=[CH:26][N:45]=3)[C:51]2=[O:54])[CH:5]=[CH:6][C:7]=1[F:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 542286423-Iodo-1-trityl-1H-1,2,4-triazoleHCID 67534032HCID 67534032, compound

Product 1

HCID 86761624HCID 86761624, compound

Reagents, catalysts & solvents 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To 5-(3-chloro-4-fluorophenyl)-3-methyl-1-pyrimidin-2-yl-1,3-dihydro-2H-indol-2-one (648 mg, 1.76 mmol), 1-trityl-3-iodo-1,2,4-triazole (809 mg, 1.85 mmol, prepared using similar procedures as described in U.S. Pat. No. 5,393,732 incorporated herein by reference in its entirety. Potassium carbonate (1071 mg, 7.75 mmol), N,N′-dimethylethylenediamine (0.300 mL, 2.82 mmol) and copper (I) iodide (268 mg, 1.41 mmol) under nitrogen was added toluene (15 mL). The mixture was stirred at 100° C. for 18 hours. The mixture was cooled and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 25S, eluting with 0-100% ethyl acetate/hexanes, to afford -(3-chloro-4-fluorophenyl)-3-methyl-1-pyrimidin-2-yl-1,3-dihydro-2H-indol-2-one as a white solid.

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel Biotage 25S
  4. washeluting with 0-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-26a6c283c19644e2ba161daf6840f0ee
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08273749B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes