Formic Acid → HCID 178522771, compound

HRID 1408422Notes

Reaction equation

HRID 1408422 reaction equation
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:22]=[CH:21][NH:20][N:19]=2)=[CH:14][C:13]=1[CH2:23][NH2:24]>ClCCl>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:22]=[CH:21][NH:20][N:19]=2)=[CH:14][C:13]=1[CH2:23][NH:24][CH:5]=[O:7]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 178509482HCID 178509482, compound2×

Product 1

HCID 178522771HCID 178522771, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of acetic anhydride (0.82 mL, 9.7 mmol) and formic acid (0.4 mL, 9.7 mmol) was heated to 50° C. for 30 minutes and then cooled to 0° C. 2-Chloro-5-(1H-pyrazol-3-yl)benzenemethanamine (i.e. the product of Step C) (1.0 g, 4.8 mmol) was added, and the reaction mixture was stirred at ambient temperature for 4 h. The reaction mixture was then diluted with dichloromethane, washed with saturated sodium bicarbonate solution and brine, then dried (Na2SO4) and concentrated. The crude residue was purified by preparative thin layer chromatography (TLC) (2% methanol in chloroform as eluant) to provide the title product as a solid (0.5 g).

Workup

  1. temperaturecooled to 0° C
  2. washwashed with saturated sodium bicarbonate solution and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified by preparative thin layer chromatography (TLC) (2% methanol in chloroform as eluant)

Sources & evidence

ORD record
ord-10f3669d15684a3db4937a6e0b5bb830
Source dataset
uspto-grants-2014_12
Patent number
US08921360B2

Reaction notes

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