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 1969628ノート

反応式

HRID 1969628 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-d2e1799da4ce4c19b0bc5bf0685317eb
出典データセット
uspto-grants-2013_04
特許番号
US08426411B2

反応ノート

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