Triethylamine → HCID 67439459, compound

HRID 1664868Notes

Reaction equation

HRID 1664868 reaction equation
C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.[CH2:30]([CH:33]1[CH2:39][CH2:38][CH:37]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[C:41]=2[F:47])[CH2:36][NH:35]/[C:34]/1=[N:48]\[NH2:49])[CH:31]=[CH2:32].[F:50][C:51]([F:57])([F:56])[CH2:52][C:53](O)=O>C(#N)C.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[CH2:30]([CH:33]1[CH2:39][CH2:38][CH:37]([C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[C:41]=2[F:47])[CH2:36][N:35]2[C:53]([CH2:52][C:51]([F:57])([F:56])[F:50])=[N:49][N:48]=[C:34]12)[CH:31]=[CH2:32]

Participants

9

Reactant 5

HCID 8471Triethylamine2×HCID 181649HOAt2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 27779723,3,3-Trifluoropropionic acid2×HCID 178438879HCID 178438879, compound

Product 1

HCID 67439459HCID 67439459, compoundYield 72.6%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

Triethylamine (142 μL, 1.02 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (196 mg, 1.02 mmol), and 1-hydroxy-7-azabenzotriazole (139 mg, 1.02 mmol) were added to a solution of (2Z)-3-allyl-6-(2,3-difluorophenyl)azepan-2-one hydrazone (285 mg, 1.02 mmol) and 3,3,3-trifluoropropanoic acid (90 μL, 1.02 mmol) in acetonitrile (25 mL). After 18 h, additional triethylamine (0.14 mL, 1.02 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (100 mg, 0.52 mmol), 1-hydroxy-7-azabenzotriazole (70 mg, 0.51 mmol) and 3,3,3-trifluoropropanoic acid (45 μL, 0.51 mmol) were added. After 5.5 h, the reaction mixture was heated to 60° C. After 2.5 h, the mixture was cooled to ambient temperature. After 18 h, the reaction mixture was diluted with ethyl acetate and saturated aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate, washed with saturated brine, dried with sodium sulfate, filtered and concentrated. Purification by reverse phase HPLC (100% water→100% acetonitrile with 0.1% trifluoroacetic acid) gave the title compounds (275 mg). MS 372.1 (M+1).

Workup

  1. waitAfter 5.5 h
  2. waitAfter 2.5 h
  3. temperaturethe mixture was cooled to ambient temperature
  4. waitAfter 18 h
  5. extractionThe mixture was extracted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by reverse phase HPLC (100% water→100% acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-02f284a9a8444148af95707f2f5515a3
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

Loading…