1,2-Dichloroethane → 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-((1-methyl-1H-pyrazol-4-yl)methylamino)pyrimidine-5-carboxamide

HRID 533483Notes

Reaction equation

HRID 533483 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][N:13]([CH3:15])[CH:14]=2)[C:5]([C:16]([OH:18])=O)=[CH:4][N:3]=1.[CH:19]1[CH:20]=[CH:21][C:22]2[N:27]([OH:28])[N:26]=[N:25][C:23]=2[CH:24]=1.C(Cl)CCl.[NH3:33]>CN(C=O)C>[N:27]1([O:28][C:2]2[N:7]=[C:6]([NH:8][CH2:9][C:10]3[CH:11]=[N:12][N:13]([CH3:15])[CH:14]=3)[C:5]([C:16]([NH2:33])=[O:18])=[CH:4][N:3]=2)[C:22]2[CH:21]=[CH:20][CH:19]=[CH:24][C:23]=2[N:25]=[N:26]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 580988432-chloro-4-((1-methyl-1H-pyrazol-4-yl)methylamino)pyrimidine-5-carboxylic acid

Product 1

HCID 668414732-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-((1-methyl-1H-pyrazol-4-yl)methylamino)pyrimidine-5-carboxamideYield 76.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-4-((1-methyl-1H-pyrazol-4-yl)methylamino)pyrimidine-5-carboxylic acid (1 g, 3.74 mmol) and HOBt*H2O (858 mg, 5.61 mmol) in DMF (10 mL), EDC (1.08 g, 5.61 mmol) was added. The mixture was stirred at room temperature for 30 min. Ammonia (0.5 M in dioxane, 15 mL, and 7.5 mmol) was added. It was stirred at room temperature overnight. Dioxane was removed under vacuum, the residue was added water to induce precipitation and the resulting solids were isolated by filtration to give 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-((1-methyl-1H-pyrazol-4-yl)methylamino)pyrimidine-5-carboxamide (1.04 g). MS 366.4 (M+H).

Workup

  1. stirringIt was stirred at room temperature overnight
  2. customDioxane was removed under vacuum
  3. additionthe residue was added water
  4. customprecipitation
  5. customthe resulting solids were isolated by filtration

Sources & evidence

ORD record
ord-c51dbb4bfb604814b2c7ce3e8affb877
Source dataset
uspto-grants-2014_10
Patent number
US08853230B2

Reaction notes

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