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Sodium Hydroxide → N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]pyrrolo[1,2-c]pyrimidine-3-carboxamide Hydrochloride

HRID 25156
ノート
印刷プレビュー

反応式

HRID 25156 の反応式
Cl.[CH:2]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:6]2[CH:5]=[C:4]([C:11]([OH:13])=O)[N:3]=1.C1(P([Cl:28])(C2C=CC=CC=2)=O)C=CC=CC=1.Cl.Cl.[NH2:31][C@@H:32]1[CH:37]2[CH2:38][CH2:39][N:34]([CH2:35][CH2:36]2)[CH2:33]1.[OH-].[Na+]>C1COCC1>[ClH:28].[N:34]12[CH2:39][CH2:38][CH:37]([CH2:36][CH2:35]1)[C@@H:32]([NH:31][C:11]([C:4]1[N:3]=[CH:2][N:7]3[CH:8]=[CH:9][CH:10]=[C:6]3[CH:5]=1)=[O:13])[CH2:33]2
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 73910Diphenylphosphinic chlorideHCID 12494972(R)-(+)-3-Aminoquinuclidine DihydrochlorideHCID 69607058Pyrrolo[1,2-c]pyrimidine-3-carboxylic acid hydrochloride

生成物 1

HCID 69773092N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]pyrrolo[1,2-c]pyrimidine-3-carboxamide Hydrochloride収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Pyrrolo[1,2-c]pyrimidine-3-carboxylic acid hydrochloride (0.33 g, 1.66 mmol) and TEA (2.0 mL, 14.35 mmol) are dissolved in 15 mL THF. Diphenylphosphinic chloride (0.47 g, 1.99 mmol) is added dropwise. After 1 h, (R)-(+)-3-aminoquinuclidine dihydrochloride is added and the reaction is allowed to stir at RT. After 1 day, 1N NaOH is added and the mixture is extracted with CHCl3. The combined organic layers are dried (MgSO4), filtered and concentrated. The residue is purified by chromatography (Biotage 40S, 90:9:1 CHCl3/MeOH/NH4OH) to afford 0.45 g (100%) of product. The hydrochloride salt is prepared and recrystallized from CH3CN/Et2O.

後処理

  1. waitAfter 1 day
  2. extractionthe mixture is extracted with CHCl3
  3. dry with materialThe combined organic layers are dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography (Biotage 40S, 90:9:1 CHCl3/MeOH/NH4OH)

出典と根拠

ORDレコード
ord-4bcf1dbee79d43acbf8b6721c5e60614
出典データセット
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06858613B2

反応ノート

読み込み中…

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