Isopropanol → HCID 58883330, compound

HRID 1817121Notes

Reaction equation

HRID 1817121 reaction equation
N[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([Cl:13])[CH:8]=2)[N:5]=[C:4]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[N:3]=1.CC(O)C.N(OCCC(C)C)=O>C1COCC1>[Cl:13][C:9]1[CH:8]=[C:7]([N:6]2[CH:2]=[N:3][C:4]([NH:14][C:15]3[CH:16]=[CH:17][C:18]([S:21]([NH2:24])(=[O:22])=[O:23])=[CH:19][CH:20]=3)=[N:5]2)[CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 8053Isoamyl NitriteHCID 58883350HCID 58883350, compound

Product 1

HCID 58883330HCID 58883330, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 250 mg of 4-[5-amino-1-(2-chloro-pyridin-4-yl)-1H-[1,2,4]triazol-3-ylamino]-benzenesulfonamide (0.686 mmol, 1 equiv) in 40 mL of 1:1 THF:iPrOH, 160 mg of isoamyl nitrite (1.37 mmol, 2 equiv) was added. The dark yellow solution was stirred for 12 h at 25° C. and then heated under reflux for 6 h. The reaction mixture was cooled and concentrated in vacuo. The resulting yellow solid was triturated with methanol and filtered to give the title compound as a yellow solid (118.9 mg, 50%); 1H NMR (400 MHz, (CD3)2SO) δ 10.20 (1H, s), 9.42 (1H, s), 8.55 (1H, d, J=5.6), 8.07 (1H, m), 7.95 (1H, dd, J=5.6 and 1.8), 7.77 (4H, m) and 7.18 (2H, s); MS (ES+) m/e 351.36, (ES−) m/e 349.48

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 h
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated in vacuo
  5. customThe resulting yellow solid was triturated with methanol
  6. filtrationfiltered

Sources & evidence

ORD record
ord-25b532cfebd1411da8d1f3c55965aa2a
Source dataset
uspto-grants-2009_10
Patent number
US07598245B2

Reaction notes

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