Hydrochloric Acid → 3-(2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-10-yl)pyridin-2(1H)-one

HRID 1629236Notes

Reaction equation

HRID 1629236 reaction equation
F[C:2]1[C:7]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][N:14]4[CH:18]=[C:19]([C:21]5[N:25]([CH:26]([CH3:28])[CH3:27])[N:24]=[CH:23][N:22]=5)[N:20]=[C:13]4[C:12]=3[CH:29]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.C[O:32]CCOC>>[CH:26]([N:25]1[C:21]([C:19]2[N:20]=[C:13]3[C:12]4[CH:29]=[C:8]([C:7]5[C:2](=[O:32])[NH:3][CH:4]=[CH:5][CH:6]=5)[CH:9]=[CH:10][C:11]=4[O:17][CH2:16][CH2:15][N:14]3[CH:18]=2)=[N:22][CH:23]=[N:24]1)([CH3:28])[CH3:27]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 80711,2-DimethoxyethaneHCID 5820492510-(2-fluoropyridin-3-yl)-2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

Product 1

HCID 582045463-(2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-10-yl)pyridin-2(1H)-oneYield 55%

Conditions

Temperature
80 °C

Procedure

To a solution of 10-(2-fluoropyridin-3-yl)-2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (0.047 g, 0.12 mmol) in DME (2 mL) was added 10% aq HCl (2 mL). The reaction mixture was allowed to stir and heat at 80° C. for 18 hours before cooling and concentrating under reduced pressure. The crude material was dissolved in DMF and purified by reverse phase HPLC to provide 203 (25 mg, 55%). 1H NMR (400 MHz, DMSO) δ 11.82 (s, 1H), 8.88 (d, J=2.3, 1H), 7.92 (d, J=6.7, 2H), 7.67 (ddd, J=9.0, 7.7, 2.2, 2H), 7.38 (d, J=4.8, 1H), 7.07 (d, J=8.6, 1H), 6.31 (t, J=6.7, 1H), 5.81 (dt, J=13.2, 6.6, 1H), 4.54 (q, J=5.8, 4H), 1.48 (d, J=6.6, 6H). MS (ESI(+)): m/z 389.1 (M+H)

Workup

  1. temperaturebefore cooling
  2. concentrationconcentrating under reduced pressure
  3. dissolutionThe crude material was dissolved in DMF
  4. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-32472e7e101a476c948c6265b5c9fc61
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

Loading…