5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde → 2-[4-[2-[2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3H-pyran-2-yl]ethyl]-2-fluoro-phenyl]-2-methyl-propanenitrile

HRID 858634ノート

反応式

HRID 858634 の反応式
[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([CH3:26])([CH3:25])[C:23]#[N:24])=[C:18]([F:27])[CH:17]=3)[CH2:11][C:10](=[O:12])[CH2:9][C:8](=[O:13])[O:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:28][C:29]1[CH:34]=[C:33]([CH3:35])[N:32]2[N:36]=[C:37]([CH:39]=O)[N:38]=[C:31]2[N:30]=1>CO>[CH:1]1([C:6]2([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:26])[C:23]#[N:24])=[C:18]([F:27])[CH:17]=3)[CH2:11][C:10]([OH:12])=[C:9]([CH2:39][C:37]3[N:38]=[C:31]4[N:30]=[C:29]([CH3:28])[CH:34]=[C:33]([CH3:35])[N:32]4[N:36]=3)[C:8](=[O:13])[O:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 236352265,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehydeHCID 587624232-{4-[2-(2-cyclopentyl-4,6-dioxotetrahydro-2H-pyran-2-yl)ethyl]-2-fluorophenyl)-2-methylpropanenitrile

生成物 1

HCID 547088342-[4-[2-[2-cyclopentyl-5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3H-pyran-2-yl]ethyl]-2-fluoro-phenyl]-2-methyl-propanenitrile

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 2-{4-[2-(2-cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-2-fluoro-phenyl}-2-methyl-propionitrile (0.40 g, 1.1 mmol) in MeOH (7 mL) was added 5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde (0.19 g, 1.08 mmol) and borane-dimethylamine complex (76 mg, 1.3 mmol) and stirred at room temperature for 3 hours. The reaction was quenched with 10 mL saturated NH4Cl and 5 mL water. To this was added 20 mL CH2Cl2 and the pH of the aqueous phase was adjusted to 3. The layers were separated, and the aqueous layer was extracted with 3×30 mL 10% MeOH in CH2Cl2. The organic layers were combined, and dried over Na2SO4. After filtering off the solids, the liquid was concentrated by rotary evaporation to an oil. The oil was flash chromatographed, and the resulting product was further purified by preparatory HPLC. Yield: 28 mg, 5%. MS (ESI): 530 (M−H).

後処理

  1. customThe reaction was quenched with 10 mL saturated NH4Cl and 5 mL water
  2. additionTo this was added 20 mL CH2Cl2
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with 3×30 mL 10% MeOH in CH2Cl2
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtering off the solids
  7. concentrationthe liquid was concentrated by rotary evaporation to an oil
  8. customchromatographed
  9. customthe resulting product was further purified by preparatory HPLC

出典と根拠

ORDレコード
ord-e8600871e80541959721fa1967f27487
出典データセット
uspto-grants-2006_12
特許番号
US07148226B2

反応ノート

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