Sodium Hydroxide → 6-chloro-N-(3-chloro-4-methoxyphenyl)-N'-cycloheptyl-[1,3,5]triazine-2,4-diamine

HRID 1375518Notes

Reaction equation

HRID 1375518 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12](OC)=[C:11](Cl)[CH:10]=2)[N:5]=[C:4]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([Cl:27])[CH:20]=2)[N:3]=1.Cl[C:29]1C=C(NC2N=C(Cl)N=C(Cl)N=2)C=CC=1OC.[OH-].[Na+]>>[Cl:1][C:2]1[N:3]=[C:4]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([Cl:27])[CH:20]=2)[N:5]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:29][CH2:11][CH2:10]2)[N:7]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 21896921(3-Chloro-4-methoxy-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine2×HCID 21897041HCID 21897041, compound

Product 1

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

Procedure

Attempts to minimize the impurity involved scanning several bases and solvents, but the production 6-chloro-N-(3-chloro-4-methoxyphenyl)-N′-(3-chloro-4-methoxyphenyl)[1,3,5]triazine-2,4-diamine remained. The preparation of compound 101 was then carried out without addition of base, resulting in the levels of the impurity being negligible. Compound 133 was prepared from compound 101 using aqueous NaOH as base.

Workup

  1. additionwas then carried out without addition of base
  2. customresulting in the levels of the impurity

Sources & evidence

ORD record
ord-635ae682cb8548f0b06160fc1c6500d1
Source dataset
uspto-grants-2007_01
Patent number
US07169785B2

Reaction notes

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