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

HRID 1623065노트

반응식

HRID 1623065 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:25](=[CH:26][CH:27]=1)[CH2:24][C@@:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[N:8](COCC[Si](C)(C)C)[C:7]1=[O:23])[CH2:5]2.Cl.C(N)CN.[OH-].[Na+]>CO.O>[NH2:1][C:2]1[CH:3]=[C:4]2[C:25](=[CH:26][CH:27]=1)[CH2:24][C@@:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]1=[O:23])[CH2:5]2

참가 물질

7

반응물 4

HCID 313Hydrochloric Acid2회HCID 3301EthylenediamineHCID 14798Sodium HydroxideHCID 67016448HCID 67016448, 화합물

생성물 1

HCID 54776259(S)-5-amino-1,3-dihydrospiro[indene-2,3-pyrrolo[2,3-b]pyridin]-2(1H)-one

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

A solution of (S)-5-amino-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one from Step B (13.7 g, 35.9 mmol) in methanol (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 (2.4 mL, 35.9 mmol) and 10 N sodium hydroxide (7.2 mL, 72 mmol) to adjust the mixture to pH 10. After 30 min, the mixture was diluted with H2O (400 mL) and extracted with CHCl3 (2×1 L). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was triturated with MeOH (50 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 (2×1 L)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was triturated with MeOH (50 mL)

출처 및 근거

ORD 기록
ord-55953fe27c12487da402545c1356bb4a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778957B2

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