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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
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HRID 25156 반응식
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
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참가 물질

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반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4bcf1dbee79d43acbf8b6721c5e60614
출처 데이터셋
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06858613B2

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