Ether hydrochloride → 2-tert-Butyl-1-(cyclohexylmethyl)-N-methyl-1H-benzimidazol-5-amine

HRID 472935ノート

反応式

HRID 472935 の反応式
[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([NH:21][C:22](=O)OC)=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.CCOCC.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([C:5]1[N:9]([CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:8]2[CH:17]=[CH:18][C:19]([NH:21][CH3:22])=[CH:20][C:7]=2[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 10953452Ether hydrochlorideHCID 11588208Methyl [2-tert-butyl-1-(cyclohexylmethyl)-1H-benzimidazol-5-yl]carbamateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 116307962-tert-Butyl-1-(cyclohexylmethyl)-N-methyl-1H-benzimidazol-5-amine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Methyl [2-tert-butyl-1-(cyclohexylmethyl)-1H-benzimidazol-5-yl]carbamate (650 mg, 1.89 mmol) was dissolved in 20 mL of THF at 0° C. under nitrogen. 1M HCl/ether (2.65 mL, 2.65 mmol) was added dropwise and the solution was stirred at 0° C. for 15 min. LiAlH4 (360 mg, 9.45 mmol) was then slowly added and the solution was stirred at rt overnight. The reaction mixture was quenched at 0° C. by addition of MeOH (5 mL) followed by water (10 mL). The solution was diluted with EtOAc and washed with saturated NaHCO3 solution, brine and dried over anhydrous MgSO4. The solvent was evaporated and the product was used directly for Step A without further purification. Yield: 544 mg (96%). 1H NMR (400 MHz, CHLOROFORM-D) δ 1.08 (s, 2H), 1.17 (m, 3H), 1.54 (s, 9H), 1.64 (m, 2H), 1.67 (m, 2H), 1.72 (m, 2H), 2.02 (m, 1H), 2.87 (s, 3H), 4.06 (d, J=7.62 Hz, 2H), 6.60 (dd, J=8.69, 2.25 Hz, 1H), 7.00 (d, J=1.76 Hz, 1H), 7.12 (d, J=8.59 Hz, 1H).

後処理

  1. stirringthe solution was stirred at rt overnight
  2. customThe reaction mixture was quenched at 0° C. by addition of MeOH (5 mL)
  3. additionThe solution was diluted with EtOAc
  4. washwashed with saturated NaHCO3 solution, brine
  5. dry with materialdried over anhydrous MgSO4
  6. customThe solvent was evaporated
  7. customthe product was used directly for Step A without further purification

出典と根拠

ORDレコード
ord-80d2963645324f42aa4f45bc051d9a04
出典データセット
uspto-grants-2014_01
特許番号
US08633235B2

反応ノート

読み込み中…