Benzylamine → 4-(8-benzyl-7-oxo-6,7,8,9-tetrahydro-5H-imidazo[1,5-a][1,4]diazepin-5-yl)-benzonitrile

HRID 15419Notes

Reaction equation

HRID 15419 reaction equation
[CH:1]([C:3]1[N:7]([CH:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[CH2:9][C:10]([O:12]C)=O)[CH:6]=[N:5][CH:4]=1)=O.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:22]([N:29]1[C:10](=[O:12])[CH2:9][CH:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[N:7]2[CH:6]=[N:5][CH:4]=[C:3]2[CH2:1]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 17975636Methyl 3-[5-formyl-imidazol-1-yl]-3-(4-cyano-phenyl)-propionate

Product 1

HCID 99974924-(8-benzyl-7-oxo-6,7,8,9-tetrahydro-5H-imidazo[1,5-a][1,4]diazepin-5-yl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of the title C compound, methyl 3-[5-formyl-imidazol-1-yl]-3-(4-cyano-phenyl)-propionate (0.22 g, 0.78 mmol) in DCE (5 mL) is added benzylamine (0.100 mL, 0.92 mmol) followed by sodium triacetoxyborohydride (0.49 g, 2.3 mmol). The reaction mixture is stirred at RT for 16 h, then partitioned between EtOAc and saturated aqueous sodium bicarbonate, and the organic solution is washed with brine, dried (anhydrous sodium sulfate) and concentrated. The residue is subjected to flash chromatography (silica) eluting with EtOAc:MeOH:NH4OH (90:10:1) to give 4-(8-benzyl-7-oxo-6,7,8,9-tetrahydro-5H-imidazo[1,5-a][1,4]diazepin-5-yl)-benzonitrile: m.p. 65° C.; e/z (ES) 343 (M+1, 100%).

Workup

  1. custompartitioned between EtOAc and saturated aqueous sodium bicarbonate
  2. washthe organic solution is washed with brine
  3. dry with materialdried (anhydrous sodium sulfate)
  4. concentrationconcentrated
  5. washeluting with EtOAc:MeOH:NH4OH (90:10:1)

Sources & evidence

ORD record
ord-44960f5c65a6459b8a36e6bd3cfa7881
Source dataset
uspto-grants-2010_06
Patent number
US07732603B2

Reaction notes

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