Trichloroacetic Acid → HCID 86680158, compound

HRID 1915959Notes

Reaction equation

HRID 1915959 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]([NH:5][C@H:6]1[C:12](=[CH:13][O:14]C)[CH2:11][CH2:10][N:9]([C:16]2[N:17]([CH3:24])[N:18]=[CH:19][C:20]=2[N+:21]([O-:23])=[O:22])[CH2:8][CH2:7]1)=[O:4].ClC(Cl)(Cl)C(O)=O>C(Cl)(Cl)Cl>[F:25][C:2]([F:1])([F:26])[C:3]([NH:5][C@H:6]1[CH:12]([CH:13]=[O:14])[CH2:11][CH2:10][N:9]([C:16]2[N:17]([CH3:24])[N:18]=[CH:19][C:20]=2[N+:21]([O-:23])=[O:22])[CH2:8][CH2:7]1)=[O:4]

Participants

4

Reactant 2

HCID 6421Trichloroacetic Acid2×HCID 86680156HCID 86680156, compound

Product 1

HCID 86680158HCID 86680158, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2,2,2-trifluoro-N-[(4R)-5-(methoxymethylene)-1-(2-methyl-4-nitro-pyrazol-3-yl)azepan-4-yl]acetamide (1060 mg, 2.81 mmol) in chloroform (90 mL) was added trichloroacetic acid (1.84 g, 11.24 mmol). The mixture was heated at 70° C. overnight and another portion of trichloroacetic acid (1.84 g, 11.24 mmol) was added and heating continued for 6 h. After cooling to room temperature, the reaction was quenched with saturated sodium bicarbonate and extracted with DCM 3×. The combined organic layers were concentrated and the residue was purified via silica gel column chromatography (0-100% EA/heptane) to give 2,2,2-trifluoro-N-[(4R)-5-formyl-1-(2-methyl-4-nitro-pyrazol-3-yl)azepan-4-yl]acetamide (896 mg, 88%).

Workup

  1. temperatureheating
  2. temperatureAfter cooling to room temperature
  3. customthe reaction was quenched with saturated sodium bicarbonate
  4. extractionextracted with DCM 3×
  5. concentrationThe combined organic layers were concentrated
  6. customthe residue was purified via silica gel column chromatography (0-100% EA/heptane)

Sources & evidence

ORD record
ord-c0fce1d854314a319a05cf567bb1e87e
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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