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

HRID 1783892노트

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HRID 1783892 반응식
CO[C:3](=O)[NH:4][C:5]1[CH:24]=[CH:23][C:8]2[N:9]([CH2:16][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[N:11][C:7]=2[CH:6]=1.Cl.CCOCC.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:12]([C:10]1[N:9]([CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:8]2[CH:23]=[CH:24][C:5]([NH:4][CH3:3])=[CH:6][C:7]=2[N:11]=1)([CH3:15])([CH3:13])[CH3:14]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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 stirred at 0° C. for 15 min. LiAlH4 (360 mg, 9.45 mmol) was then slowly added and the solution 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 aqueous solution, brine and dried over anhydrous MgSO4. The solvent was evaporated and the product was used directly in the next step without further purification. Yield: 544 mg (96%). 1H NMR (400 MHz, CHLOROFORM-D) δ 1.08 (m, 2H), 1.17 (m, 3H), 1.53 (s, 9H), 1.64 (s, 2H), 1.67 (s, 2H), 1.72 (m, 2H), 2.02 (m, 1H), 2.86 (s, 3H), 4.06 (d, J=7.42 Hz, 2H), 6.60 (dd, J=8.69, 2.25 Hz, 1H), 6.99 (d, J=2.15 Hz, 1H), 7.12 (d, J=8.59 Hz, 1H).

후처리

  1. stirringthe solution 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 aqueous solution, brine
  5. dry with materialdried over anhydrous MgSO4
  6. customThe solvent was evaporated
  7. customthe product was used directly in the next step without further purification

출처 및 근거

ORD 기록
ord-d46b3c62044847c4bcb3f8670203ab74
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07501447B2

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