Hydrochloric Acid → HCID 58204951, compound

HRID 1498093Notes

Reaction equation

HRID 1498093 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]=[CH:19][N:20]=[C:13]4[C:12]=3[CH:21]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.C[O:24]CCOC>>[N:20]1[CH:19]=[CH:18][N:14]2[C:13]=1[C:12]1[CH:21]=[C:8]([C:7]3[C:2](=[O:24])[NH:3][CH:4]=[CH:5][CH:6]=3)[CH:9]=[CH:10][C:11]=1[O:17][CH2:16][CH2:15]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 80711,2-DimethoxyethaneHCID 5820489610-(2-Fluoropyridin-3-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

Product 1

HCID 58204951HCID 58204951, compound

Conditions

Temperature
80 °C

Procedure

To a solution of 10-(2-fluoropyridin-3-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine (100 mg, 0.4 mmol) in DME (4 mL) was added 10% aqueous HCl (4 mL). The reaction was allowed to stir and heated at 80° C. overnight. The reaction was allowed to cool to room temperature and concentrated under reduced pressure. The crude was purified by Prep HPLC to provide 3-(5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-10-yl)pyridin-2(1H)-one. LC/MS (ESI+): m/z 280 (M+H). 1H NMR (500 MHz, DMSO) δ 11.73 (s, 1H), 8.71 (d, J=2.3, 1H), 7.72-7.50 (m, 1H), 7.47-7.21 (m, 1H), 7.15-6.86 (m, 2H), 6.29 (t, J=6.6, 1H), 4.44 (d, J=6.1, 4H).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe crude was purified by Prep HPLC

Sources & evidence

ORD record
ord-b8b09d87d6f04d3c962ffec32072c060
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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