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Ammonium formate → 6-(4-oxo-2-phenoxymethyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-5-yl)-3',4',5',6'-tetrahydro-2'H-[2,4']bipyridinyl-1'-carboxylic acid tert-butyl ester

HRID 2046228
ノート
印刷プレビュー

反応式

HRID 2046228 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N:20]3[CH2:25][CH2:24][N:23]4[N:26]=[C:27]([CH2:29][O:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH:28]=[C:22]4[C:21]3=[O:37])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N:20]3[CH2:25][CH2:24][N:23]4[N:26]=[C:27]([CH2:29][O:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH:28]=[C:22]4[C:21]3=[O:37])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 574100246-(4-oxo-2-phenoxymethyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-5-yl)-3',6'-dihydro-2'H-[2,4']bipyridinyl-1'-carboxylic acid tert-butyl ester

生成物 1

HCID 679916106-(4-oxo-2-phenoxymethyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-5-yl)-3',4',5',6'-tetrahydro-2'H-[2,4']bipyridinyl-1'-carboxylic acid tert-butyl ester収率 87.4%

試薬・触媒・溶媒 2

HCID 23938Palladium
触媒
HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

10% Palladium on charcoal (11 mg, 0.01 mmol) was added to a stirred suspension of 6-(4-oxo-2-phenoxymethyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-5-yl)-3′,6′-dihydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (51 mg, 0.10 mmol) and ammonium formate (38 mg, 0.61 mmol) in MeOH (0.5 mL) in a sealed tube and under nitrogen. The mixture was stirred at 80° C. for 30 minutes. The mixture was filtered through a pad of diatomaceous earth and washed with DCM. The filtrate was treated with brine and extracted with more DCM. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 50/50). The desired fractions were collected and the solvents evaporated in vacuo to yield 6-(4-oxo-2-phenoxymethyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-5-yl)-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (44 mg, 86% yield) as a yellow oil.

後処理

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth
  2. washwashed with DCM
  3. additionThe filtrate was treated with brine
  4. extractionextracted with more DCM
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvents evaporated in vacuo
  9. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 50/50)
  10. customThe desired fractions were collected
  11. customthe solvents evaporated in vacuo

出典と根拠

ORDレコード
ord-2de923f6c0884faca72e4c5b2e520222
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08592422B2

反応ノート

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