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

HRID 2055301Notes

Reaction equation

HRID 2055301 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-e38b3a8c68a744b39b98bbf9ffc17240
Source dataset
uspto-grants-2008_02
Patent number
US07332488B2

Reaction notes

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