Hydrochloric Acid → HCID 88385605, compound

HRID 1488566Notes

Reaction equation

HRID 1488566 reaction equation
Cl.[NH2:2][CH:3]([C:14](=[O:31])[CH2:15][CH2:16][C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=1)[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[C:32]1(=[O:38])[O:37][C:35](=[O:36])[CH2:34][CH2:33]1.Cl.[OH-].[Na+:41]>CN(C1C=CN=CC=1)C.C(N(CC)CC)C.ClCCl>[Na+:41].[F:30][C:27]([F:28])([F:29])[C:19]1[CH:18]=[C:17]([CH2:16][CH2:15][C:14](=[O:31])[CH:3]([NH:2][C:32](=[O:38])[CH2:33][CH2:34][C:35]([O-:37])=[O:36])[CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][CH:6]=2)[CH:22]=[C:21]([C:23]([F:25])([F:24])[F:26])[CH:20]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 14798Sodium HydroxideHCID 22905844HCID 22905844, compound

Product 1

HCID 88385605HCID 88385605, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
-78 °C

Procedure

To a mixture of the compound of part (e) (215 mg) and dichloromethane (3 ml) cooled to -78° C. under argon, was added with stirring dry triethylamine (70 μl). To the resulting solution was added succinic anhydride (50 mg) and 4-dimethylaminepyridine (5 mg), and the mixture was allowed to warm to room temperature. The mixture was stirred at room temperature for a further 3 hours before pouring into aqueous 2N hydrochloric acid (4 ml). The organic layer was separated, and the aqueous layer extracted with ethyl acetate. The combined organic layers were dried (MgSO4) and evaporated. The residue was treated with one equivalent of aqueous sodium hydroxide, sufficient acetonitrate added to render the mixture homogeneous, and the resulting solution freeze dried. The resulting solid was dissolved in ethyl acetate (1 ml) and petroleum ether (10 ml) added. The mixture was boiled to half volume, and the solid product collected by filtration, and dried in-vacuo to afford the title compound. 1N NMR (360 MHz; D6 -DMSO) δ2.15 (2H, m), 2.25 (2H, m), 2.72 (1H, m), 2.87 (4H, m), 3.05 (1H, dd, J=5.7, 14.5 Hz), 4.42 (1H, m), 6.97 (1H, t, J=7.8 Hz), 7.05 (1H, t, J=8.0 Hz), 7.18 (1H, d, J=2.2 Hz), 7.32 (1H, d, J=8.3 Hz), 7.48 (1H, d, J=7.7 Hz), 7.79 (2H, s), 7.85 (1H, s), 9.00 (1H, d, J=6.8 Hz), 10.90 (1H, s); m/e (CI+) 528 (MH+). Found: C, 52.12; H, 3.99; N, 4.67. C25H21F6 N2O4Na.1.5(H2O) requires C, 52.00; H, 4.19; N, 4.85%.

Workup

  1. additionwas added
  2. temperatureto warm to room temperature
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. customevaporated
  7. additionadded to render the mixture homogeneous
  8. customthe resulting solution freeze dried
  9. dissolutionThe resulting solid was dissolved in ethyl acetate (1 ml)
  10. additionpetroleum ether (10 ml) added
  11. filtrationthe solid product collected by filtration
  12. customdried in-vacuo

Sources & evidence

ORD record
ord-6e06797fe73c4176ae456722115caa21
Source dataset
uspto-grants-1997_10
Patent number
US05674889

Reaction notes

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