Sodium Hydroxide → HCID 21897115, compound

HRID 916117Notes

Reaction equation

HRID 916117 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]([O:16][CH3:17])=[C:12]([F:18])[CH:11]=2)[N:3]=1.[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:8][C:6]1[N:7]=[C:2]([NH:22][CH:19]2[CH2:21][CH2:20]2)[N:3]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([F:18])[CH:11]=2)[N:5]=1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 69828Cyclopropylamine2×HCID 516951Monobasic potassium phosphateHCID 21897051HCID 21897051, compound

Product 1

HCID 21897115HCID 21897115, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolvent2×HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To 124 (2.01 g, 7.0 mmol) dissolved in acetone (40 mL) was added a solution of cyclopropylamine (0.5 mL, 7 mmol) in acetone (5 mL) followed by addition of NaOH (2.8 mL, 2.5 N, 7.0 mmol) and 8 mL of water. The reaction was stirred and heated at reflux for 3 hours. The reaction mixture was poured over crushed ice. The solid that formed was collected by vacuum filtration and was dried overnight under vacuum to afford unpurified E10 (1.8 g). {A separate reaction [124, (2.00 g, 7 mmol) and cyclopropylamine (0.5 mL, 7 mmol)] yielded unpurified E10 (1.9 g).} The two lots (1.8 g and 1.9 g) were combined for purification. Column chromatography (50:50 v:v hexane:ethyl acetate) yielded a faint yellow solid (E10) (2.89 g, 67%); mp 186° C.; HPLC: Inertsil ODS 3V C18, 40:30:30 [KH2PO4 (0.01 M, pH 3.2): CH3OH:CH3CN], 264 nm, Rt 16.6 min, 94.9% purity; MS (TOF ES+) m/z 310 (M+H, 100), 312 (44.4).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. additionThe reaction mixture was poured
  4. customover crushed ice
  5. customThe solid that formed
  6. filtrationwas collected by vacuum filtration
  7. customwas dried overnight under vacuum
  8. customto afford unpurified E10 (1.8 g)
  9. customyielded unpurified E10 (1.9 g)
  10. custom} The two lots (1.8 g and 1.9 g) were combined for purification
  11. customColumn chromatography (50:50 v:v hexane:ethyl acetate) yielded a faint yellow solid (E10) (2.89 g, 67%)

Sources & evidence

ORD record
ord-076e794250a04848af589b9a3f18264c
Source dataset
uspto-grants-2007_09
Patent number
US07268134B2

Reaction notes

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