Sodium Hydroxide → HCID 21896983, compound

HRID 1374025Notes

Reaction equation

HRID 1374025 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[C:15](Cl)[N:14]=[C:13]([Cl:18])[N:12]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH:19]1([NH2:22])[CH2:21][CH2:20]1.[OH-].[Na+].OP([O-])(O)=O.[K+]>CC(C)=O.CC#N.CO.O>[Cl:18][C:13]1[N:12]=[C:11]([NH:10][C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=2)[N:16]=[C:15]([NH:22][CH:19]2[CH2:21][CH2:20]2)[N:14]=1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 516951Monobasic potassium phosphateHCID 21896921(3-Chloro-4-methoxy-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine

Product 1

HCID 21896983HCID 21896983, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolvent2×HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To 101 (2.01 g, 6.5 mmol) dissolved in acetone (35 mL) was added a solution of cyclopropylamine (0.45 mL, 6.5 mmol) in acetone (5 mL) followed by addition of NaOH (2.6 mL, 2.5 N, 7.0 mmol) and 6.5 mL of water. The reaction mixture was stirred and heated at reflux for 3 hours. The reaction mixture was extracted 3 times with dichloromethane; the combined organic layers were washed with brine and dried over potassium carbonate. The sample was filtered, concentrated, and dried overnight under vacuum. Column chromatography (50:50 v:v hexane:ethyl acetate) yielded a faint yellow solid (E13) (1.12 g, 53%); mp 172° C.; HPLC: Inertsil ODS 3V C18, 40:30:30 [KH2PO4 (0.01 M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 24.6 min, 99% purity; MS (TOF ES+) m/z 328 (72.6), 326 (M+H, 100).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. extractionThe reaction mixture was extracted 3 times with dichloromethane
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over potassium carbonate
  6. filtrationThe sample was filtered
  7. concentrationconcentrated
  8. customdried overnight under vacuum
  9. customColumn chromatography (50:50 v:v hexane:ethyl acetate) yielded a faint yellow solid (E13) (1.12 g, 53%)

Sources & evidence

ORD record
ord-57b1dd79a19c400bb732ac81574dd19f
Source dataset
uspto-grants-2007_01
Patent number
US07163943B2

Reaction notes

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