Trifluoroacetic acid → HCID 58497206, compound

HRID 1254025Notes

Reaction equation

HRID 1254025 reaction equation
[I:1][C:2]1[N:6]([CH3:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[N:4][C:3]=1[C:14]1[CH:23]=[CH:22][C:17]([C:18]([NH:20][NH2:21])=[O:19])=[CH:16][CH:15]=1.[C:24](O)(C(F)(F)F)=O>C(OCC)(OCC)OCC>[I:1][C:2]1[N:6]([CH3:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[N:4][C:3]=1[C:14]1[CH:23]=[CH:22][C:17]([C:18]2[O:19][CH:24]=[N:21][N:20]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66986330HCID 66986330, compound

Product 1

HCID 58497206HCID 58497206, compound

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Conditions

Temperature
130 °C

Procedure

4-(5-Iodo-1-methyl-2-pyridin-2-yl-1H-imidazol-4-yl)benzohydrazide (4.9 g, 12 mmol) was suspended in 60 mL of triethyl orthoformate, to which was added 1 mL of TFA. The suspension was heated at 130° C. The reaction was cooled to rt, and the precipitate was collected, washed with hexanes and dried to give 4.8 g of the title compound. 1H NMR (500 MHz, (CDCl3): 8.62 (m, 1H), 8.57 (s, 1H), 8.11 (m, 1H), 8.09 (s, 4H), 7.82 (m, 1H), 7.32 (m, 1H), 4.13 (s, 3H). LCMS: [M+1]=430.

Workup

  1. temperatureThe reaction was cooled to rt
  2. customthe precipitate was collected
  3. washwashed with hexanes
  4. customdried

Sources & evidence

ORD record
ord-f2ba9226166d47ca9bd641320d32fbda
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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