Triethylamine → 7-methoxy-8-phenylmethoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine

HRID 536214ノート

反応式

HRID 536214 の反応式
[CH2:1]([O:8][C:9]1[C:10]([O:21][CH3:22])=[C:11]([C:13]([C:16]2[NH:17][CH2:18][CH2:19][N:20]=2)=[CH:14][CH:15]=1)[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([N:25](CC)CC)C.N#CBr>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH2:1]([O:8][C:9]1[CH:15]=[CH:14][C:13]2[C:16]3[N:20]([CH2:19][CH2:18][N:17]=3)[C:23]([NH2:25])=[N:12][C:11]=2[C:10]=1[O:21][CH3:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 70592683-(benzyloxy)-6-(4,5-dihydro-1H-imidazol-2-yl)-2-methoxyaniline

生成物 1

HCID 1784938207-methoxy-8-phenylmethoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
0 °C

実験手順

A mixture of 3-(benzyloxy)-6-(4,5-dihydro-1H-imidazol-2-yl)-2-methoxyaniline (Step 6, 100 g, 336 mmol) and triethylamine (188 mL) in DCM (3 L) was cooled to 0° C. and treated with cyanogen bromide (78.4 g, 740 mmol). The reaction mixture was stirred and allowed to warm to room temperature gradually. After 16 h the reaction mixture was diluted with a solution of saturated sodium bicarbonate and extracted with DCM. The organic layer was washed three times with saturated bicarbonate solution followed by multiple washes with brine. The organic layer was dried (sodium sulfate) and concentrated under reduced pressure to give a semi solid (130 g with triethylamine salt contamination): 1H NMR (DMSO-d6) δ: 7.30-7.48 (7H, m), 5.31 (2H, s), 4.32 (2H, m), 4.13 (2H, m), 3.81 (3H, s).

後処理

  1. temperatureto warm to room temperature gradually
  2. extractionextracted with DCM
  3. washThe organic layer was washed three times with saturated bicarbonate solution
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customto give a semi solid (130 g with triethylamine salt contamination)

出典と根拠

ORDレコード
ord-53a580880bea4798bb327cf1936b8a44
出典データセット
uspto-grants-2014_10
特許番号
US08859572B2

反応ノート

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