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Ammonium Chloride → 9-(Tert-butyl)-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

HRID 532959
Notes
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Reaction equation

HRID 532959 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]1[C:16](=[O:17])[CH2:15][NH:14][C:13](=[O:18])[CH:12]=[C:7]12.F[B-](F)(F)F.[CH:24]1([C:30]2NC=C[N+]=2C2CCCCC2)[CH2:29]CCC[CH2:25]1.C([Mg]Cl)(C)(C)C.[NH4+].[Cl-]>C1COCC1.Cl[Ni]Cl>[C:24]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]1[C:16](=[O:17])[CH2:15][NH:14][C:13](=[O:18])[CH:12]=[C:7]12)([CH3:30])([CH3:29])[CH3:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 867113289-Bromo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dioneHCID 89621986Dicyclohexylimidazolium tetrafluoroborateHCID 178418310HCID 178418310, compound

Product 1

HCID 867114029-(Tert-butyl)-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dioneYield 50%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

125-1. A mixture of 9-bromo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione (2.0 g, 6.51 mmol), NiCl2*2H2O (0.43 g, 2.60 mmol) and dicyclohexylimidazolium tetrafluoroborate (0.83 g, 2.60 mmol) in THF (80 mL) was cooled to −20° C. and then treated with a 1M solution of tBuMgCl (39.0 mL, 39.0 mmol) dropwise. The mixture was allowed to slowly warm to RT, then poured onto a saturated aq. solution of NH4Cl and extracted with AcOEt. The combined org. layers were then dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (SiO2, heptane to AcOEt to AcOEt/MeOH 95:5) afforded the title compound (370 mg). UPLC-MS: MS 285.2 (M+H+); UPLC rt 0.91 min.

Workup

  1. temperatureto slowly warm to RT
  2. extractionextracted with AcOEt
  3. dry with materiallayers were then dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (SiO2, heptane to AcOEt to AcOEt/MeOH 95:5)

Sources & evidence

ORD record
ord-28b5aee625c14fce8c1b552b8c8cc002
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08853203B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes