Dichloromethane → HCID 68674364, compound

HRID 2196074Notes

Reaction equation

HRID 2196074 reaction equation
C(P(CCCC)CCCC)CCC.C1COCC1.[OH:19][C:20]1[CH:39]=[CH:38][C:23]2[N:24]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:25](=[O:33])[C:26]([CH3:32])([CH3:31])[C:27](=[O:30])[N:28]([CH3:29])[C:22]=2[CH:21]=1.[N:40]1[CH:45]=[CH:44][CH:43]=[C:42]([CH2:46][CH2:47][N:48]([CH2:53][C:54]2[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=2)[CH2:49][CH2:50][CH2:51]O)[CH:41]=1.[Cl:60]CCl>O>[ClH:60].[ClH:60].[ClH:60].[CH2:34]([N:24]1[C:25](=[O:33])[C:26]([CH3:31])([CH3:32])[C:27](=[O:30])[N:28]([CH3:29])[C:22]2[CH:21]=[C:20]([O:19][CH2:51][CH2:50][CH2:49][N:48]([CH2:47][CH2:46][C:42]3[CH:41]=[N:40][CH:45]=[CH:44][CH:43]=3)[CH2:53][C:54]3[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=3)[CH:39]=[CH:38][C:23]1=2)[CH:35]([CH3:36])[CH3:37]

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 13831TributylphosphineHCID 50943225HCID 50943225, compoundHCID 669609373-[(2-Pyridin-3-ylethyl)pyridin-4-ylmethylamino]propan-1-ol

Product 1

HCID 68674364HCID 68674364, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N,N,N′,N′-Tetramethylazodicarboxamide(TMAD) (189 mg, 1.1 mmol) and tri-n-butyl phosphine (0.28 ml, 1.1 mmol) were added to a THF solution (5 ml) of 7-hydroxy-1-isobutyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (213 mg, 0.73 mmol) and 3-[(2-pyridin-3-ylethyl)pyridin-4-ylmethylamino]propan-1-ol (199 mg, 0.73 mmol), and stirred at room temperature overnight. Water was added to the reaction mixture, and extraction with dichloromethane was performed. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1→10:1). The purified product was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane:methanol=40:1→10:1) again. The purified product was concentrated under reduced pressure. A 4N-hydrogen chloride ethyl acetate solution (0.57 ml) was added to the residue (ethyl acetate solution), stirred at room temperature for 30 minutes, and concentrated to dryness under reduced pressure to thereby obtain 480 mg (yield: quantitative) of 1-isobutyl-3,3,5-trimethyl-7-{3-[(2-pyridin-3-ylethyl)pyridin-4-ylmethylamino]propoxy}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione trihydrochloride as a white amorphous solid.

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1→10:1)
  4. concentrationThe purified product was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (dichloromethane:methanol=40:1→10:1) again
  6. concentrationThe purified product was concentrated under reduced pressure
  7. additionA 4N-hydrogen chloride ethyl acetate solution (0.57 ml) was added to the residue (ethyl acetate solution)
  8. stirringstirred at room temperature for 30 minutes
  9. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9c2f925b18e6475ab35d927337006128
Source dataset
uspto-grants-2012_12
Patent number
US08338406B2

Reaction notes

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