Water → 5-(-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyloxy)pyrazine-2-carbonitrile

HRID 1969628노트

반응식

HRID 1969628 반응식
[CH2:1]([CH:3]1[CH:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][N:17](COCC[Si](C)(C)C)[C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][CH:5]([O:28][C:29]2[N:30]=[CH:31][C:32]([C:35]#[N:36])=[N:33][CH:34]=2)[CH2:4]1)[CH3:2].C(O)(C(F)(F)F)=O.[OH-].[NH4+].O>C(Cl)Cl>[CH2:1]([CH:3]1[CH:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][NH:17][C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][CH:5]([O:28][C:29]2[N:30]=[CH:31][C:32]([C:35]#[N:36])=[N:33][CH:34]=2)[CH2:4]1)[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 585574165-(3-ethyl-4-(6-((2-(trimethyl silyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyloxy)pyrazine-2-carbonitrile

생성물 1

HCID 1360095685-(-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyloxy)pyrazine-2-carbonitrile수율 88.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 5-(3-ethyl-4-(6-((2-(trimethyl silyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyloxy)pyrazine-2-carbonitrile (0.097 g, 0.19 mmol, Preparation #11.1) in DCM (2.5 mL) was added TFA (0.7 mL, 10 mmol). The reaction mixture was stirred at ambient temperature for about 1.5 h. The solvents were removed under reduced pressure and the residue was dissolved in 1,4-dioxane (1.3 mL). Ammonium hydroxide (28-30% aqueous ammonia, 2.5 mL, 24 mmol) was added and the reaction mixture was heated at about 60° C. for about 30 min then cooled to ambient temperature. Water (4 mL) was added and the precipitate was collected by filtration to give 5-(-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyloxy)pyrazine-2-carbonitrile (0.0628 g, 87%): LC/MS (Table 1, Method b) Rt=1.99 min; MS m/z: 375 (M+H)+.

후처리

  1. customThe solvents were removed under reduced pressure
  2. dissolutionthe residue was dissolved in 1,4-dioxane (1.3 mL)
  3. temperaturethe reaction mixture was heated at about 60° C. for about 30 min
  4. temperaturethen cooled to ambient temperature
  5. filtrationthe precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-d2e1799da4ce4c19b0bc5bf0685317eb
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426411B2

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