1,1'-Carbonyldiimidazole → 1-(4-(2-Aminopyrimidin-4-yloxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1 H-pyrazol-5-yl)urea

HRID 2069152노트

반응식

HRID 2069152 반응식
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[C:13]([C:17]1[CH:21]=[C:20]([NH2:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)[N:18]=1)([CH3:16])([CH3:15])[CH3:14].[NH2:30][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]([O:41][C:42]2[CH:47]=[CH:46][N:45]=[C:44]([NH2:48])[N:43]=2)=[CH:33][CH:32]=1>C(Cl)Cl>[NH2:48][C:44]1[N:43]=[C:42]([O:41][C:34]2[C:35]3[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:31]([NH:30][C:6]([NH:22][C:20]3[N:19]([C:23]4[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=4)[N:18]=[C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:21]=3)=[O:7])=[CH:32][CH:33]=2)[CH:47]=[CH:46][N:45]=1

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 29741323-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amineHCID 207688484-(4-Aminonaphthalen-1-yloxy)pyrimidin-2-amine

생성물 1

HCID 585647671-(4-(2-Aminopyrimidin-4-yloxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1 H-pyrazol-5-yl)urea

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To a suspension of CDI (17.24 g, 106 mmol) in DCM (150 mL) was added 3-tert-butyl-1-p-tolyl-1H-pyrazol-5-amine (24.38 g, 106 mmol) in 1 g portions over 40 min and the reaction stirred at RT for 2 hr. An aliquot of this solution (5.0 mL,) was added dropwise to a suspension of 4-(4-aminonaphthalen-1-yloxy)pyrimidin-2-amine (720 mg, 2.85 mmol) in DCM (15 mL) and the mixture maintained at RT for 2 hr. The reaction mixture was diluted with DCM (20 mL) and was washed with water (30 mL) and brine (30 mL) and then dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, EtOAc in isohexane, 20-60%, gradient elution) to afford the title compound, Intermediate P1, as a beige solid (1.21 g, 83%); Rt 2.12 min (Method 2); m/z 508 (M+H)+, (ES+)+.

후처리

  1. temperaturethe mixture maintained at RT for 2 hr
  2. washwas washed with water (30 mL) and brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography (SiO2, EtOAc in isohexane, 20-60%, gradient elution)

출처 및 근거

ORD 기록
ord-028e52a3706244c89489050c2b0fd5fc
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299074B2

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