Water → HCID 59659975, compound

HRID 2057063Notes

Reaction equation

HRID 2057063 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][C:13]([CH3:16])=[C:12]([F:17])[CH:11]=2)[N:3]=1.[CH:18]1([NH2:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[OH-].[Na+].O>CC(C)=O>[Cl:8][C:6]1[N:7]=[C:2]([NH:25][CH:18]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[N:3]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([F:17])[CH:11]=2)[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2899CycloheptylamineHCID 14798Sodium HydroxideHCID 58799092HCID 58799092, compound

Product 1

HCID 59659975HCID 59659975, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To 156a (1.0010 g, 3.7 mmol) dissolved in acetone (20 mL) was added a solution of N-cycloheptylamine (0.5 mL, 3.7 mmol) in acetone (5 mL) followed by addition of 2.5 N NaOH (1.5 mL, 3.7 mmol) and water (4 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, and the resulting solid was dried overnight under vacuum. Flash column chromatography (SiO2, 70:30 hexanes:ethyl acetate) yielded a white solid (156b, 1.144 g, 88%), mp 149° C.; HPLC: Inertsil ODS-3V C18, 30:70 [KH2PO4 (0.01M, pH 3.2): CH3CN], 264 nm, Rt 28.9 min, 90.4% purity; MS (TOF MS ES+): m/z 427 (40.2), 351 (32.2), 350 (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
  7. customthe resulting solid was dried overnight under vacuum

Sources & evidence

ORD record
ord-6aa7fc18103c47fd8cb995331d89b42b
Source dataset
uspto-grants-2008_02
Patent number
US07335770B2

Reaction notes

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