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Acetic Acid → 6-(3-fluorobenzyl)-1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid

HRID 628361
ノート
印刷プレビュー

反応式

HRID 628361 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=1)[CH2:5][N:6]1[C:14]2[C:9](=[N:10][C:11]([N:15](C(OC(C)(C)C)=O)[NH:16]C(OC(C)(C)C)=O)=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:31]([O:33]CC1C=CC=C(F)C=1)=[O:32].[OH-].[Na+].O.[CH3:48][C:49](O)=O>>[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=1)[CH2:5][N:6]1[C:14]2[CH:13]=[CH:48][C:49]3[N:10]([C:11]([CH3:12])=[N:15][N:16]=3)[C:9]=2[CH:8]=[C:7]1[C:31]([OH:33])=[O:32]
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 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 118159869di-tert-butyl 1-(1-(3-fluorobenzyl)-2-{[(3-fluorobenzyl)oxy]carbonyl}-1H-pyrrolo[3,2-b]pyridin-5-yl)hydrazine-1,2-dicarboxylate

生成物 1

HCID 1181598066-(3-fluorobenzyl)-1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid

実験手順

A solution of di-tert-butyl 1-(1-(3-fluorobenzyl)-2-{[(3-fluorobenzyl)oxy]carbonyl}-1H-pyrrolo[3,2-b]pyridin-5-yl)hydrazine-1,2-dicarboxylate (0.33 g, 0.54 mmol, from Step 2) in AcOH (10 mL) was heated in portions, in the microwave, to 180° C. for 10 minutes each. The reactions were pooled and AcOH was removed in vacuo. The residue was dissolved in methanol (2 mL) and 1.0 M NaOH in water (10 mL, 10 mmol) was added. When the hydrolysis reaction was complete, it was filtered, diluted with MeCN and H2O and then purified via preparative HPLC-MS (C18 eluting with a gradient of MeCN/H2O containing 0.15% NH4OH). Yield: (0.17 g, 97%). LCMS (M+H)+: 325.3.

後処理

  1. customAcOH was removed in vacuo
  2. dissolutionThe residue was dissolved in methanol (2 mL)
  3. customWhen the hydrolysis reaction
  4. filtrationit was filtered
  5. additiondiluted with MeCN and H2O
  6. custompurified via preparative HPLC-MS (C18
  7. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)

出典と根拠

ORDレコード
ord-e0ce42a56495472080a17b9b72765c97
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09309246B2

反応ノート

読み込み中…

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