Water → HCID 15524333, compound

HRID 1976696Notes

Reaction equation

HRID 1976696 reaction equation
[CH2:1]([N:8]([C:28](=[O:33])[C:29]([F:32])([F:31])[F:30])[CH2:9][CH2:10][N:11]([C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[C:20](Cl)=[CH:21][NH:22]2)[C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(=O)(O)(O)[OH:35].O>C(O)(=O)C>[CH2:1]([N:8]([C:28](=[O:33])[C:29]([F:32])([F:31])[F:30])[CH2:9][CH2:10][N:11]([C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[CH2:20][C:21](=[O:35])[NH:22]2)[C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 1004Phosphoric AcidHCID 15524334HCID 15524334, compound

Product 1

HCID 15524333HCID 15524333, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
77.5 °C

Procedure

To a solution of N-[2-(benzyl-trifluoroacetyl-amino)-ethyl]-2,2,2-trifluoro-N-(3-chloro-1H-indol-4-yl)acetamide (1.4 g, 2.85 mmol) in acetic acid (18 mL) was added a mixture of 85% phosphoric acid (10 mL) and water (3 mL). The reaction was heated at 75-80° C. for 16 hours. The mixture was poured into water (100 mL) and the crude product crystallized as a solid. After filtration, the solids were dissolved in ethyl acetate (100 mL), washed with water (50 mL), saturated sodium bicarbonate solution (50 mL) and brine (20 mL), dried over anhydrous magnesium sulfate and filtered. Purification of the residue by chromatography (silica gel, 40% hexane-ethyl acetate) and crystallization from ether-petroleum ether afforded the title compound as a white solid, (0.31 g, 23.0%), mp 108-111° C.; MS EI m/e 473 (M+).

Workup

  1. customthe crude product crystallized as a solid
  2. filtrationAfter filtration
  3. dissolutionthe solids were dissolved in ethyl acetate (100 mL)
  4. washwashed with water (50 mL), saturated sodium bicarbonate solution (50 mL) and brine (20 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customPurification of the residue
  8. customby chromatography (silica gel, 40% hexane-ethyl acetate) and crystallization from ether-petroleum ether

Sources & evidence

ORD record
ord-69c24ced962a4487a697fc98bb37ed5c
Source dataset
uspto-grants-2001_05
Patent number
US06228880B1

Reaction notes

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