Cyanuric chloride → n-[2-Benzyloxy-4-(4,6-dichloro-[1,3,5]triazin-2-ylamino)-phenyl]-4-fluoro-2-hydroxy-benzamide

HRID 1354821Notes

Reaction equation

HRID 1354821 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:18])[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[OH:17])=[C:4]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:3]=1.C([O-])(O)=O.[Na+].[N:32]1[C:39]([Cl:40])=[N:38][C:36](Cl)=[N:35][C:33]=1[Cl:34]>C1COCC1>[CH2:20]([O:19][C:4]1[CH:3]=[C:2]([NH:1][C:36]2[N:38]=[C:39]([Cl:40])[N:32]=[C:33]([Cl:34])[N:35]=2)[CH:7]=[CH:6][C:5]=1[NH:8][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[OH:17])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 516892Sodium BicarbonateHCID 21104164N-(4-Amino-2-benzyloxy-phenyl)-4-fluoro-2-hydroxy-benzamide

Product 1

HCID 21103874n-[2-Benzyloxy-4-(4,6-dichloro-[1,3,5]triazin-2-ylamino)-phenyl]-4-fluoro-2-hydroxy-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-(4-Amino-2-benzyloxy-phenyl)-4-fluoro-2-hydroxy-benzamide (76) (0.060 g, 0.170 mmol) was dissolved in THF (3.4 mL), NaHCO3 (0.086 g, 1.02 mmol) was added and the mixture was chilled on a dry-ice/acetone bath. Cyanuric chloride (5) (0.032 g, 0.184 mmol) was dissolved in THF (2 mL) and added directly to the chilled solution while stirring. The ice bath was removed and the mixture continued to stir while warming to room temperature for 1 h. TLC (Rf: 0.8 compared to Rf: 0.35 for compound 76 in 1:1 hexane/EtOAc, single spot) indicated complete reaction at this point. The reaction mixture was used immediately in the next step without purification or characterization.

Workup

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

Sources & evidence

ORD record
ord-07bde3f379b04a55a44a6548c2e6319c
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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