Water → HCID 59659970, compound

HRID 2057065Notes

Reaction equation

HRID 2057065 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)[N:3]=1.[CH:19]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[OH-].[Na+].O>CC(C)=O>[Cl:8][C:6]1[N:7]=[C:2]([NH:26][CH:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:3]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=2)[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2899CycloheptylamineHCID 14798Sodium HydroxideHCID 372837HCID 372837, compound

Product 1

HCID 59659970HCID 59659970, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To 158a (1.0008 g, 3.5 mmol) dissolved in acetone (20 mL) was added a solution of N-cycloheptylamine (0.45 mL, 3.5 mmol) in acetone (5 mL) followed by addition of 2.5 N NaOH (1.4 mL, 3.5 mmol) and water (3.5 mL). The reaction mixture was allowed to stir at reflux for 3 hours under nitrogen. The reaction mixture was extracted 2 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 yellow solid (158b, 991 mg, 78%), mp 82° C.; HPLC: Inertsil ODS-3V C18, 40:10:50 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 54.5 min, 99.8% purity; MS (TOF MS ES+): m/z 440 (100), 365 (20.0), 363 (M+H, 53.2).

Workup

  1. temperatureat reflux for 3 hours under nitrogen
  2. extractionThe reaction mixture was extracted 2 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-f45a1ccae4a448a0890c9343f571d14d
Source dataset
uspto-grants-2008_02
Patent number
US07335770B2

Reaction notes

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