Acetic Acid → 2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-8-ol

HRID 886405Notes

Reaction equation

HRID 886405 reaction equation
Cl[C:2]1[N:23]=[CH:22][C:5]2[C:6]3[N:7]([CH:11]=[C:12]([C:14]4[N:18]([CH:19]([CH3:21])[CH3:20])[N:17]=[CH:16][N:15]=4)[N:13]=3)[CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1.C(O)(=[O:26])C>>[CH:19]([N:18]1[C:14]([C:12]2[N:13]=[C:6]3[C:5]4=[CH:22][NH:23][C:2](=[O:26])[CH:3]=[C:4]4[O:10][CH2:9][CH2:8][N:7]3[CH:11]=2)=[N:15][CH:16]=[N:17]1)([CH3:21])[CH3:20]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 582045209-chloro-2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepine

Product 1

HCID 1360309132-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a,9-triaza-benzo[e]azulen-8-ol

Conditions

Temperature
155 °C

Procedure

A solution of 2.64 g (8.00 mmol) of 9-chloro-2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepine 317 in 250 ml of glacial acetic acid was placed into 350 ml glass pressure vessel. The vessel was closed and the mixture was heated for 64 hours at 155° C. The mixture was cooled down to room temperature. White precipitate appeared. The mixture was concentrated to 50 ml volume in vacuum, the solid material was filtered out, washed with acetic acid, ethyl ether and dried on air. Weight 1.68 g. The above product was stirred with 15 ml of sat NaHCO3 for 1 hour, filtered out, washed with 2×10 ml of water, dissolved in THF/water (10:1) mixture and concentrated. The residue was dried in high vacuum for 18 hours to give 2-(1-Isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[3,4-f][1,4]oxazepin-9(10H)-one. Yield 1.12 g (45%). M/z 313.1, calc. 312.13. 1H NMR (400 MHz, DMSO) δ 11.79 (s, 1H), 8.41 (s, 1H), 7.89 (s, 1H), 7.82 (s, 1H), 5.84 (s, 1H), 5.78 (dt, J=13.2, 6.6, 1H), 4.57-4.51 (m, 2H), 4.50-4.45 (m, 2H), 1.45 (d, J=6.6, 6H)

Workup

  1. customThe vessel was closed
  2. temperatureThe mixture was cooled down to room temperature
  3. concentrationThe mixture was concentrated to 50 ml volume in vacuum
  4. filtrationthe solid material was filtered out
  5. washwashed with acetic acid, ethyl ether
  6. customdried on air
  7. filtrationfiltered out
  8. washwashed with 2×10 ml of water
  9. dissolutiondissolved in THF/water (10:1) mixture
  10. concentrationconcentrated
  11. customThe residue was dried in high vacuum for 18 hours

Sources & evidence

ORD record
ord-79a79b61023a4259bba27ef8fa28f50b
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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