Dimethylformamide → HCID 67340621, compound

HRID 1668440Notes

Reaction equation

HRID 1668440 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=1)=[CH:7]2)([O-:3])=[O:2].Cl.Cl[CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH3:31].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.C(OCC)(=O)C>[CH2:28]([N:29]([CH2:32][CH3:33])[CH2:30][CH2:31][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:7]=[C:8]1[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][C:21]([F:24])([F:22])[F:23])=[CH:18][CH:19]=1)[CH3:27]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 59004647HCID 59004647, compound

Product 1

HCID 67340621HCID 67340621, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

Compound 8 (77 mg, 0.229 mmol), 2-chloro-N,N-diethylethanamine hydrochloride (43.3 mg, 0.252 mmol), potassium carbonate (95 mg, 0.687 mmol) and anhydrous dimethylformamide (5 mL) were charged to a small, argon purged flask fitted with a magnetic stirbar and resulting solution heated in an oil bath at 65° C. for 2 hours. After cooling to room temperature the mixture was diluted with H2O and ethyl acetate, transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with brine (twice), dried over magnesium sulphate, filtered and concentrated to afford crude solid. The crude product was purified via chromatography on silica gel (2M NH3 in MeOH:CH2Cl2, 2.5:97.5) to yield compound 9 (79 mg, 79.2%) as a yellow solid. 1H NMR (DMSO-d6) δ 0.77 (t, 6H, J=7.1 Hz), 2.39 (q, 4H, J=7.2 Hz), 2.50 (m, 2H), 4.19 (t, 2H, J=6.5 Hz), 4.31 (s, 2H), 6.40 (s, 1H), 7.33-7.41 (m, 4H), 7.58 (d, 1H, J=9.1 Hz), 7.99 (dd, 1H, J=9.0, 2.2 Hz), 8.48 (d, 1H, J=2.3 Hz).

Workup

  1. customfitted with a magnetic stirbar
  2. customresulting solution
  3. temperatureAfter cooling to room temperature the mixture
  4. customtransferred to a separatory funnel
  5. customthe organic layer collected
  6. extractionThe aqueous layer was further extracted with ethyl acetate
  7. washthe combined organic layers were washed with brine (twice),
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto afford crude solid
  12. customThe crude product was purified via chromatography on silica gel (2M NH3 in MeOH:CH2Cl2, 2.5:97.5)

Sources & evidence

ORD record
ord-17e52b901b08470094d9278f6fae8118
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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