Cyanuric chloride → N-[2-Benzyloxy-4-(4,6-dichloro-[1,3,5]triazin-2-ylamino)-phenyl]-acetamide

HRID 1354856Notes

Reaction equation

HRID 1354856 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:3]=1.C([O-])(O)=O.[Na+].[N:25]1[C:32]([Cl:33])=[N:31][C:29](Cl)=[N:28][C:26]=1[Cl:27]>C1COCC1>[CH2:13]([O:12][C:4]1[CH:3]=[C:2]([NH:1][C:29]2[N:31]=[C:32]([Cl:33])[N:25]=[C:26]([Cl:27])[N:28]=2)[CH:7]=[CH:6][C:5]=1[NH:8][C:9](=[O:11])[CH3:10])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 516892Sodium BicarbonateHCID 14166615HCID 14166615, compound

Product 1

HCID 21103875N-[2-Benzyloxy-4-(4,6-dichloro-[1,3,5]triazin-2-ylamino)-phenyl]-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-(4-Amino-2-benzyloxy-phenyl)-acetamide (399) (0.65 g, 2.54 mmol) and NaHCO3 (1.28 g, 15.24 mmol) were suspended in THF (100 mL) and chilled on a dry-ice/acetone bath. The cyanuric chloride (5) (0.465 g, 2.54 mmol) was dissolved in THF (4 mL) and added to the chilled solution. The ice-bath was removed and the mixture was stirred while warming to room temperature over a period of 45 minutes. TLC (Rf: 0.6 compared to Rf: 0.1 for compound 399 and Rf: 0.95 for compound 400 in 1:1 hexane/EtOAc, single spot) indicated complete reaction at this point. This reaction mixture was used directly in the next step without further purification or characterization.

Workup

  1. temperaturechilled on a dry-ice/acetone bath
  2. additionadded to the chilled solution
  3. customThe ice-bath was removed
  4. customreaction at this point
  5. customThis reaction mixture was used directly in the next step without further purification or characterization

Sources & evidence

ORD record
ord-6d1eea9b07f74b74b6a943c0333ef69b
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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