Water → HCID 69461264, compound

HRID 1297118Notes

Reaction equation

HRID 1297118 reaction equation
[Li+].CC([N-]C(C)C)C.C1COCC1.[CH2:14]([N:16]1[C:22]2[CH:23]=[C:24]([O:29][CH3:30])[C:25]([O:27][CH3:28])=[CH:26][C:21]=2[C:20]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N:19][CH2:18][C:17]1=[O:37])[CH3:15].[N+:38]([C:41]1[CH:48]=[CH:47][CH:46]=[CH:45][C:42]=1[CH2:43]Br)([O-:40])=[O:39].O>C1COCC1>[CH3:28][O:27][C:25]1[C:24]([O:29][CH3:30])=[CH:23][C:22]2[N:16]([CH2:14][CH3:15])[C:17](=[O:37])[CH:18]([CH2:43][C:42]3[CH:45]=[CH:46][CH:47]=[CH:48][C:41]=3[N+:38]([O-:40])=[O:39])[N:19]=[C:20]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:21]=2[CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77569alpha-Bromo-2-nitrotolueneHCID 10997623Lithium diisopropylamide mono(tetrahydrofuran)HCID 69461240HCID 69461240, compound

Product 1

HCID 69461264HCID 69461264, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 920 μl (1.84 mmol) of 2M LDA/THF in 5 ml of anhydrous THF, add dropwise at −78° C. under an inert atmosphere a solution of 300 mg (0.92 mmol) of 1-ethyl-7,8-dimethoxy-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (IIbd) in 2 ml of THF. Allow to equilibrate to room temperature for 30 minutes. Add dropwise at −30° C. a solution of 220 mg (1.01 mmol) of 2-nitrobenzyl bromide in 2 ml of THF. Stir at room temperature for 12 hours. Add 1 ml of H2O. Evaporate the THF. Purify by silica chromatography (AcOEt 1/hexane 4, 1/1, then AcOEt). Recrystallize in EtOH/cHexane. Yield: 35%. M: 158–160° C. 1H-NMR (DMSO, 300 MHz): d 0.87–0.91 (m, 3H, CH3), 3.61–3.99 (m, 10H, NCH+CHCH2+2OCH3), 4.35–4.40 (m, 1H, NCH), 6.60 (s, 1H Ar), 6.82 (s, 1 H Ar), 7.37–7.90 (m, 9H Ar). Mass: (M+H)+=460.88.

Workup

  1. customEvaporate the THF
  2. customPurify by silica chromatography (AcOEt 1/hexane 4, 1/1
  3. customRecrystallize in EtOH/cHexane
  4. custom158–160° C

Sources & evidence

ORD record
ord-a00ba59825d348269d2e3566080be1b9
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

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