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Hydrochloric Acid → (R)-5-Amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 552557
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HRID 552557 반응식
[O:1]=[C:2]1[N:10](COCC[Si](C)(C)C)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@:3]21[CH2:26][C:25]1[C:20](=[CH:21][CH:22]=[C:23]([NH:27]C(=O)OC(C)(C)C)[CH:24]=1)[CH2:19]2.Cl.C(N)CN.[OH-].[Na+]>CO.O>[NH2:27][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[CH2:19][C@:3]1([C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:10][C:2]1=[O:1])[CH2:26]2
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참가 물질

7

반응물 4

HCID 313Hydrochloric Acid2회HCID 3301EthylenediamineHCID 14798Sodium HydroxideHCID 73013404(R)-tert-butyl 2'-oxo-1'-((2-(trimethylsilyl)ethoxy)methyl)-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridine]-5-ylcarbaMate

생성물 1

HCID 53260812(R)-5-Amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

A solution of tert-butyl(R)-(2′-oxo-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-yl)carbamate from Step C (13.4 g, 27.8 mmol) in MeOH (300 mL) was saturated with HCl (g). The mixture was resaturated with HCl (g) every 30 min until the starting material was consumed, and then concentrated in vacuo. The residue was dissolved in MeOH (150 mL) and treated with ethylenediamine (1.9 mL, 27.8 mmol) and 10 N sodium hydroxide (6 mL, 60 mmol) to adjust the mixture to pH 10. After 30 min, the mixture was diluted with H2O (400 mL) and extracted with CHCl3 (1 L). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was triturated with MeOH (35 mL) to give the title compound. MS: m/z=252 (M+1).

후처리

  1. customwas consumed
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in MeOH (150 mL)
  4. extractionextracted with CHCl3 (1 L)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was triturated with MeOH (35 mL)

출처 및 근거

ORD 기록
ord-579bab9926ab4fe7a65c76d33bedf0c7
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07951795B2

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