Ammonia → 3-[3-(4-Amino-[1,3,5]triazin-2-yl)-pyridin-2-ylamino]-N-(4-phenoxy-phenyl)benzamide

HRID 983450Notes

Reaction equation

HRID 983450 reaction equation
Cl[C:2]1[C:7]([C:8]2[N:13]=[CH:12][N:11]=[C:10]([NH:14]C3C=C(OC)C(OC)=C(OC)C=3)[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.N.[NH2:28][C:29]1[CH:30]=[C:31]([CH:48]=[CH:49][CH:50]=1)[C:32]([NH:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:37][CH:36]=1)=[O:33]>CS(C)=O>[NH2:14][C:10]1[N:11]=[CH:12][N:13]=[C:8]([C:7]2[C:2]([NH:28][C:29]3[CH:30]=[C:31]([CH:48]=[CH:49][CH:50]=3)[C:32]([NH:34][C:35]3[CH:36]=[CH:37][C:38]([O:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)=[CH:39][CH:40]=3)=[O:33])=[N:3][CH:4]=[CH:5][CH:6]=2)[N:9]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 161090054-(2-chloropyridin-3-yl)-N-(3,4,5-trimethoxyphenyl)-1,3,5-triazin-2-amineHCID 225600953-Amino-N-(4-phenoxyphenyl)benzamide

Product 1

HCID 101625493-[3-(4-Amino-[1,3,5]triazin-2-yl)-pyridin-2-ylamino]-N-(4-phenoxy-phenyl)benzamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

[4-(2-Chloro-pyridin-3-yl)-[1,3,5]triazin-2-yl]-(3,4,5-trimethoxy-phenyl)amine (Example 2, Step 4) (247 mg, 1.08 mmol) was suspended in a 2 M solution of NH3 in IpOH (3 ml)(Aldrich), and the reaction mixture was stirred overnight in a sealed tube. Concentration, trituration in a small amount of MeOH, and filtration provided a white solid. A portion of this material (97 mg, 0.47 mmol) was mixed with 3-amino-N-(4-phenoxyphenyl)benzamide (320 mg, 0.96 mmol) and DMSO (250 ml), and stirred overnight at 90° C. The dark residue was diluted with IpOH, sonicated, triturated, and then concentrated. Upon dilution with IpOH, a light green solid was isolated by filtration. MS m/z=476.5. [M+H]+. Calc'd for C27H21N7O2: 475.18.

Workup

  1. concentrationConcentration, trituration
  2. filtrationin a small amount of MeOH, and filtration
  3. customprovided a white solid
  4. stirringstirred overnight at 90° C
  5. additionThe dark residue was diluted with IpOH
  6. customsonicated
  7. customtriturated
  8. concentrationconcentrated
  9. customUpon dilution with IpOH, a light green solid was isolated by filtration

Sources & evidence

ORD record
ord-81e7ecd6542446169c6890c6ef5cc728
Source dataset
uspto-grants-2005_03
Patent number
US06864255B2

Reaction notes

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