Hexahydro-1,4-diazepine → HCID 19826010, compound

HRID 1086451Notes

Reaction equation

HRID 1086451 reaction equation
[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([S:17]([Cl:20])(=[O:19])=[O:18])=[CH:10][C:11]=3[C:12]2([CH3:16])[CH3:15])=[CH:4][CH:3]=1.[NH:21]1[CH2:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>C(Cl)Cl>[ClH:20].[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([S:17]([N:21]4[CH2:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)(=[O:19])=[O:18])=[CH:10][C:11]=3[C:12]2([CH3:16])[CH3:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 19826018HCID 19826018, compound

Product 1

HCID 19826010HCID 19826010, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add the product of step 2 (0.5 g, 1.3 mmol) as a suspension in methylene chloride (10 mL) to hexahydro-2H-1,4-diazepine erazine (0.16 g) in methylene chloride (5 mL) at room temperature over 5 minutes. Stir the reaction mixture for 18 hours. Add aqueous sodium hydroxide (50 mL, 0.1N) to the reaction mixture, separate, and dry the organic layer (MgSO4), filter and concentrate to the title compound free base as a white solid. Chromatograph the solid on a column of silica gel (300 g) eluting with 5:95 methanol:methylene chloride. The solid is dissolved in aqueous hydrochloric acid (50 mL, 1N), concentrated, redissolved in water (25 mL) and lyophilized to give the title compound hydrate (200 mg, 31%) as a white solid. Rf=0.30 (1:9 methanol:methylene chloride). Calculated for C20H26O3N2SCl2Br: C, 49.04; H, 5.35; N, 5.72; S, 6.53. Observed: C, 48.62; H, 4.64; N, 5.70; S, 6.52.

Workup

  1. customAdd aqueous sodium hydroxide (50 mL, 0.1N) to the reaction mixture, separate
  2. dry with materialdry the organic layer (MgSO4)
  3. filtrationfilter
  4. concentrationconcentrate to the title compound free base as a white solid
  5. washeluting with 5:95 methanol
  6. dissolutionThe solid is dissolved in aqueous hydrochloric acid (50 mL, 1N)
  7. concentrationconcentrated
  8. dissolutionredissolved in water (25 mL)

Sources & evidence

ORD record
ord-7c9a29b600d64adc9749cc19c5caf3ac
Source dataset
uspto-grants-1991_07
Patent number
US05030631

Reaction notes

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