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

HRID 15419ノート

反応式

HRID 15419 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-44960f5c65a6459b8a36e6bd3cfa7881
出典データセット
uspto-grants-2010_06
特許番号
US07732603B2

反応ノート

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