Water → HCID 59659980, compound

HRID 2057070Notes

Reaction equation

HRID 2057070 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:21]=[C:20](Cl)[N:19]=[C:18]([Cl:23])[N:17]=2)=[CH:11][C:10]=1[Cl:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25]1([NH2:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.[OH-].[Na+].O>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:21]=[C:20]([NH:32][CH:25]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[N:19]=[C:18]([Cl:23])[N:17]=2)=[CH:11][C:10]=1[Cl:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2899CycloheptylamineHCID 14798Sodium HydroxideHCID 59659978HCID 59659978, compound

Product 1

HCID 59659980HCID 59659980, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To 160b (1.0010 g, 2.6 mmol) dissolved in acetone (25 mL) was added a solution of N-cycloheptylamine (0.35 mL, 2.6 mmol) in acetone (5 mL) followed by addition of 2.5 N NaOH (1.0 mL, 2.6 mmol) and water (2.5 mL). The reaction mixture was allowed to stir at reflux for 3 hours under nitrogen. The reaction mixture was extracted 3 times with dichloromethane; the combined organic layers were washed with brine and dried over potassium carbonate. After filtering, the sample was concentrated by rotary evaporation and the resulting solid was dried overnight under vacuum. Flash column chromatography (SiO2, 70:30 hexanes:ethyl acetate) yielded a white solid (160c, 855 mg, 72%), mp 110° C.; HPLC: Inertsil ODS-3V C18, 30:70 [KH2PO4 (0.01M, pH 3.2): CH3CN], 264 nm, Rt 47.3 min, 94.7% purity; MS (TOF MS ES+): m/z 535 (44.7), 460 (73.3), 458 (M+H, 100).

Workup

  1. temperatureat reflux for 3 hours under nitrogen
  2. extractionThe reaction mixture was extracted 3 times with dichloromethane
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over potassium carbonate
  5. filtrationAfter filtering
  6. concentrationthe sample was concentrated by rotary evaporation
  7. customthe resulting solid was dried overnight under vacuum

Sources & evidence

ORD record
ord-45520f1d9f5b421d8ef53cbe538afc41
Source dataset
uspto-grants-2008_02
Patent number
US07335770B2

Reaction notes

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