Water → N-Azepan-1-yl-6-chloro-N'-(3-chloro-4-methoxy-phenyl)-[1,3,5]triazine-2,4-diamine

HRID 916104Notes

Reaction equation

HRID 916104 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[C:15]([Cl:17])[N:14]=[C:13](Cl)[N:12]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[NH2:19][N:20]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.[OH-].[Na+].O>CC(C)=O>[OH-:8].[NH4+:10].[N:20]1([NH:19][C:13]2[N:12]=[C:11]([NH:10][C:4]3[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=3)[N:16]=[C:15]([Cl:17])[N:14]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 221981-AminohomopiperidineHCID 21896921(3-Chloro-4-methoxy-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine

Product 2

HCID 14923Ammonium HydroxideHCID 21896980N-Azepan-1-yl-6-chloro-N'-(3-chloro-4-methoxy-phenyl)-[1,3,5]triazine-2,4-diamineYield 31.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To 101 (6.03 g, 20.0 mmol) dissolved in acetone (75 mL) was added a solution of 1-aminohomopiperidine (2.3 mL, 20.0 mmol) in acetone (10 mL) followed by addition of NAOH (8.0 mL 2.5 N NaOH solution, 20.0 mmol) and 20 mL of water. The reaction mixture was allowed to stir at reflux overnight 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 sample was concentrated on a rotary evaporator and the resulting oil was dried overnight under vacuum. Column chromatography (96:3:1 dichloromethane:methanol:conc. ammonium hydroxide) yielded a light purple solid 152 (1.2 g, 16%), mp 139° C.; TLC (silica gel, 96:3:1, CH2Cl2, CH3OH, conc. NH4OH), Rf 0.3 1; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01 M, pH 3.2): CH3OH:CH3CN], 264 nm, Rt 52.5 min, 94.9% purity; MS (ESI): m/z 383 (M+H, 100).

Workup

  1. temperatureat reflux overnight 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 sample was concentrated on a rotary evaporator
  6. customthe resulting oil was dried overnight under vacuum

Sources & evidence

ORD record
ord-642e5e275f16426587254a6c0fda1216
Source dataset
uspto-grants-2007_09
Patent number
US07268134B2

Reaction notes

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