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Potassium Hydroxide → 2-(5-(4-Amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid

HRID 246736
ノート
印刷プレビュー

反応式

HRID 246736 の反応式
[NH2:1][C:2]([CH3:50])([CH3:49])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[N:11]=[C:10]2[C:17]1[N:22]=[C:21]2[C:23]([C:45]([O:47]C)=[O:46])=[CH:24][N:25]([C:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:20]2=[N:19][CH:18]=1.[OH-].[K+]>O.O1CCOCC1>[NH2:1][C:2]([CH3:50])([CH3:49])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[N:11]=[C:10]2[C:17]1[N:22]=[C:21]2[C:23]([C:45]([OH:47])=[O:46])=[CH:24][N:25]([C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:20]2=[N:19][CH:18]=1
参加物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 14797Potassium HydroxideHCID 71279592methyl 2-(5-(4-amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate

生成物 1

HCID 712808552-(5-(4-Amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid収率 102.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 31275
1,4-Dioxane
溶媒

実験手順

A mixture of methyl 2-(5-(4-amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (100 mg, 0.15 mmol), potassium hydroxide (280 mg, 5 mmol) in 2.5 mL of water and 5 mL of 1,4-dioxane was heated to reflux for 90 min. The reaction mixture was cooled to room temperature, solvent evaporated, the residue diluted with H2O (25 mL) and the mixture acidified with 1N HCl to pH=7. The residue was extracted with EtOAc (100 mL). The organic layer was washed with H2O (100 mL), brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure to give 2-(5-(4-Amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid as yellow solid (100 mg, >100%) which was used to next step without further purification. LCMS: (M+H)+=651.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 90 min
  3. customsolvent evaporated
  4. additionthe residue diluted with H2O (25 mL)
  5. extractionThe residue was extracted with EtOAc (100 mL)
  6. washThe organic layer was washed with H2O (100 mL), brine (100 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-afb2fa993e4740fd893ab0986969a06e
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08658646B2

反応ノート

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