HCID 21896998, compound → (3-Chloro-4-methoxy-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine

HRID 2055300Notes

Reaction equation

HRID 2055300 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([Cl:17])[CH:10]=2)[N:5]=[C:4](NC2CCCCCC2)[N:3]=1.[Cl:26]C1N=C(NC2C=CC(OC)=C(Cl)C=2)N=C(NC2C=CC(OCC)=C(Cl)C=2)N=1>>[Cl:17][C:11]1[CH:10]=[C:9]([NH:8][C:6]2[N:5]=[C:4]([Cl:26])[N:3]=[C:2]([Cl:1])[N:7]=2)[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

3

Reactant 2

HCID 21896998HCID 21896998, compoundHCID 218970216-chloro-N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine

Product 1

HCID 21896921(3-Chloro-4-methoxy-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine

Procedure

A 1 kg campaign was conducted to develop a process which avoids multiple column purifications and employs a suitable recrystallisation method to produce compound 137. This scheme was stabilized for the campaign, however the scale up of compound 133 by one pot synthesis resulted in the formation of an impurity, which was carried over to the final step and was difficult to remove. The impurity was isolated and characterized to be 6-chloro-N-(3-chloro-4-methoxyphenyl)-N′-(3-chloro-4-ethoxyphenyl)[1,3,5]triazine-2,4-diamine. To avoid the impurity, the single pot reaction was avoided and compound 101 was isolated and purified by recrystallisation in ethylacetate.

Workup

  1. customa suitable recrystallisation method
  2. customto produce compound 137
  3. customresulted in the formation of an impurity, which
  4. customto remove
  5. customThe impurity was isolated
  6. customthe single pot reaction

Sources & evidence

ORD record
ord-3ff850cb0e8447b88262aa943e1aa5dd
Source dataset
uspto-grants-2008_02
Patent number
US07332488B2

Reaction notes

Loading…