Water → HCID 59659981, compound

HRID 2057067Notes

Reaction equation

HRID 2057067 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]([F:16])[CH:11]=2)[N:3]=1.[CH:17]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[OH-].[Na+].O>CC(C)=O>[Cl:8][C:6]1[N:7]=[C:2]([NH:24][CH:17]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[N:3]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2899CycloheptylamineHCID 14798Sodium HydroxideHCID 10747054,6-dichloro-N-(3-fluorophenyl)-1,3,5-triazin-2-amine

Product 1

HCID 59659981HCID 59659981, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To 159a (1.0016 g, 3.9 mmol) dissolved in acetone (20 mL) was added a solution of cycloheptylamine (0.5 mL, 3.9 mmol) in acetone (5 mL) followed by addition of 2.5 N NaOH (1.6 mL, 3.9 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. The filtered 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 an off-white solid (159b, 908 mg, 69%), mp 148° C.; HPLC: Inertsil ODS-3V C18, 30:70 [KH2PO4 (0.0M, pH 3.2): CH3CN], 264 nm, Rt 22.3 min, 79.2% purity; MS (TOF MS ES+): m/z 413 (60.4), 338 (44.0), 336 (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. concentrationThe filtered sample was concentrated by rotary evaporation
  6. customthe resulting solid was dried overnight under vacuum

Sources & evidence

ORD record
ord-4de904c2fe0442c48bbbb1988ad4492e
Source dataset
uspto-grants-2008_02
Patent number
US07335770B2

Reaction notes

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