Ammonia → HCID 66571317, compound

HRID 924685Notes

Reaction equation

HRID 924685 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[NH:11][C:10]([C:12]3[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=3[CH3:19])=[C:9]([C:20]#[N:21])[CH:8]=2)=[N:3][CH:2]=1.O.S(=O)(=O)(O)[OH:24].N>C(O)(C(F)(F)F)=O>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[NH:11][C:10]([C:12]3[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=3[CH3:19])=[C:9]([C:20]([NH2:21])=[O:24])[CH:8]=2)=[N:3][CH:2]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962Water2×HCID 1118Sulfuric AcidHCID 70979552HCID 70979552, compound

Product 1

HCID 66571317HCID 66571317, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-(pyrimidin-4-yl)-2-(5-chloro-2-methyl-phenyl)-1H-pyrrole-3-carbonitrile (85 mg, 0.28 mmol) in TFA (1.0 mL) were sequentially added water (0.15 mL) and 98% sulfuric acid (0.30 mL) under efficient stirring. The mixture was allowed to stir for 5 h at 70° C. and then was diluted by drop wise addition of water (1 mL). The reaction mixture was made basic (pH 10-12) by adding 30% aqueous ammonia (3 mL) under stirring. The precipitated solid was collected by filtration, washed with water and finally dried in a vacuum oven at 50° C. affording the title compound (72 mg, 83%).

Workup

  1. stirringunder stirring
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water
  4. customfinally dried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-9a752a74d7fb4a17bfba4f6950c3531f
Source dataset
uspto-grants-2016_03
Patent number
US09283224B2

Reaction notes

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