Acetic Acid → HCID 59332853, compound

HRID 1879992Notes

Reaction equation

HRID 1879992 reaction equation
[CH2:1]([C@H:8]1[CH2:14][NH:13][C:12]2[N:15]=[CH:16][CH:17]=[CH:18][C:11]=2[CH2:10][NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[Br:23]Br>C(Cl)Cl>[CH2:1]([C@H:8]1[CH2:14][NH:13][C:12]2[N:15]=[CH:16][C:17]([Br:23])=[CH:18][C:11]=2[CH2:10][NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 59332877HCID 59332877, compound

Product 1

HCID 59332853HCID 59332853, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-3-Benzyl-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepine (60 mg, 0.25 mmol) was dissolved into acetic acid (1 mL). Bromine (15 μL, 0.3 mmol) was added and the reaction was stirred overnight. Methylene chloride (10 mL) was added and the solution was washed with 1 N NaOH (1 mL) and brine (1 mL), dried over MgSO4 and concentrated. The residue was dissolved in CH2Cl2 (3 mL) and precipitated with diethyl ether. The title compound was collected as an orange solid (80 mg, 100%): 1H NMR (300 MHz, CDCl3) δ 7.96 (s, 1H), 7.42 (s, 1H), 7.37-7.17 (m, 5H), 5.42-5.00 (bs, 2H), 3.96-3.75 (m, 2H), 3.45-3.40 (m, 1H), 3.30-3.20 (m, 1H), 2.98-2.91 (m, 1H), 2.87-2.73 (m, 2H).

Workup

  1. washthe solution was washed with 1 N NaOH (1 mL) and brine (1 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in CH2Cl2 (3 mL)
  5. customprecipitated with diethyl ether
  6. customThe title compound was collected as an orange solid (80 mg, 100%)

Sources & evidence

ORD record
ord-28a0093052d44743bb682ec0a57e754e
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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