Hydrogen Bromide → 3-Amino-7-methoxy-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one

HRID 593487Notes

Reaction equation

HRID 593487 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]2[NH:7][C:8](=[O:29])[CH:9]([NH:18]C(=O)OCC3C=CC=CC=3)[N:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]=2[CH:4]=1.Br.C(OCC)C>CC(O)=O>[NH2:18][CH:9]1[C:8](=[O:29])[NH:7][C:6]2[CH:30]=[CH:31][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[N:10]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 118345108HCID 118345108, compound

Product 1

HCID 900840313-Amino-7-methoxy-5-phenyl-1H-benzo[e][1,4]diazepin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Intermediate 7B (0.5 g, 1.2 mmol) was treated with 3.5 mL (7 volumes) of 33% HBr in AcOH and was stirred at room temperature for 2 hrs. Diethyl ether (25 mL) was added to the reaction mixture and the precipitated solid was collected by filtration. The solid was dissolved in water (3 mL), and 10% sodium bicarbonate solution was added until the solution was basic. The product was extracted with 2×25 mL of ethyl acetate and the organic layer was dried over anhydrous sodium sulfate. The solvents were removed under vacuum to afford Intermediate 7C as a white solid: yield 0.32 g (98%). HPLC: RT=1.228 (H2O/ACN with NH4OAc, PUROSPHER® Star RP-18 (4×55) mm, 3 μm, gradient=3 min, wavelength=220 nm); MS(ES):m/z=282 [M+H+]; 1H NMR (DMSO-d6: δ 10.46 (brs, 1H), 7.42-7.53 (m, 5H), 7.19-7.25 (m, 2H), 6.72 (d, J=2.4 Hz, 1H), 4.25 (s, 1H), 3.39 (s, 3H).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. dissolutionThe solid was dissolved in water (3 mL)
  3. addition10% sodium bicarbonate solution was added until the solution
  4. extractionThe product was extracted with 2×25 mL of ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. customThe solvents were removed under vacuum

Sources & evidence

ORD record
ord-645985b6e8ad4938a6f47976d994ee11
Source dataset
uspto-grants-2016_01
Patent number
US09242940B2

Reaction notes

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