Potassium Carbonate → HCID 66929381, compound

HRID 1942567Notes

Reaction equation

HRID 1942567 reaction equation
[NH2:1][C:2]1[N:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)=[O:8])[N:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:31][C:32]#[N:33]>CC(=O)CC>[NH2:1][C:2]1[N:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)=[O:8])[N:5]=[C:4]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:31][C:32]#[N:33])[CH:18]=2)[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 16051513HCID 16051513, compound

Product 1

HCID 66929381HCID 66929381, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
75 °C

Procedure

Alternatively, to a solution of 5-amino-3-[3-(hydroxy)phenylamino]-1-(3-(methyl)phenyl)carbonyl-1H-1,2,4-triazole (Ia-7) (0.84 g, 2.7 mmol) in 2-butanone (9 mL) was added K2CO3 (0.41 g, 3.0 mmol) and BrCH2CN (0.36 g, 3.0 mmol). After stirring the mixture at 75° C. for 20 h, the 2-butanone was removed under reduced pressure. The residue was dissolved in EtOAc (50 mL), washed with water (50 mL), brine (30 mL), dried (Na2SO4) and concentrated to afford the crude product. Recrystallization from CH3CN afforded 5-amino-3-[3-(cyanomethoxy)phenylamino]-1-(3-(methyl)phenyl)carbonyl-1H-1,2,4-triazole (Ia-9) (0.12 g, 13%) as a white solid: Rf 0.22 (1:1 hexanes/ethyl acetate); mp (DSC) 220.0-224.4° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.45 (s, 1H), 8.05 (s, 1H), 7.91 (d, J=7.1 Hz, 1H), 7.83 (s, 2H), 7.50-7.39 (m, 3H), 7.20 (t, J=8.1 Hz, 1H), 7.12-7.09 (m, 1H), 6.56 (dd, J=7.9, 2.2 Hz, 1H), 5.04 (s, 2H), 2.43 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 166.6, 157.9, 157.2, 156.9, 142.3, 137.2, 133.0, 132.6, 130.8, 129.5, 127.8, 127.4, 116.5, 111.1, 105.2, 104.0, 53.3, 20.8; IR (ATR) 3449, 3367, 2325, 1684 cm−1; APCI MS m/z 349 [C18H16N6O2+H]+; HPLC (Method A) 96.8% (AUC), tR=12.81 min.

Workup

  1. customthe 2-butanone was removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc (50 mL)
  3. washwashed with water (50 mL), brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto afford the crude product
  7. customRecrystallization from CH3CN

Sources & evidence

ORD record
ord-88ba0bf2c4f548a19a40167f270df3de
Source dataset
uspto-grants-2013_03
Patent number
US08389557B2

Reaction notes

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