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Sodium cyanoborohydride → 9-{[3-(5-fluoro-1H-indol-3-yl)propyl]amino}-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]isoquinolin-1(8H)-one

HRID 1727393
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HRID 1727393 반응식
[NH2:1][CH:2]1[CH2:16][O:15][C:5]2=[CH:6][CH:7]=[C:8]3[C:13]([C:12](=[O:14])[NH:11][CH2:10][CH2:9]3)=[C:4]2[CH2:3]1.[F:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[C:21]2[CH2:27][CH2:28][CH:29]=O.[BH3-]C#N.[Na+]>C(O)(=O)C.CO>[F:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][CH:22]=[C:21]2[CH2:27][CH2:28][CH2:29][NH:1][CH:2]1[CH2:16][O:15][C:5]2=[CH:6][CH:7]=[C:8]3[C:13]([C:12](=[O:14])[NH:11][CH2:10][CH2:9]3)=[C:4]2[CH2:3]1
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참가 물질

6

반응물 3

HCID 5003444Sodium cyanoborohydrideHCID 118461793-(5-fluoro-1H-indol-3-yl)propanalHCID 575676709-amino-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]isoquinolin-1(8H)-one

생성물 1

HCID 462277549-{[3-(5-fluoro-1H-indol-3-yl)propyl]amino}-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]isoquinolin-1(8H)-one

시약·촉매·용매 2

HCID 176Acetic Acid용매
HCID 887
Methanol
용매

실험 절차

To a mixture of 9-amino-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]isoquinolin-1(8H)-one (46) (130 mg, 0.596 mmol), 3-(5-fluoro-1H-indol-3-yl)propanal ((2), 113 mg, 0.596 mmol) in acetic acid (70 μl) and methanol (20 ml) was added NaBH3CN (75 mg, 1.19 mmol) in portions. The resulting mixture was stirred for 2 hr. The solvent was removed in vacuo and the residue was dissolved in methylene chloride. The organic solution was washed with 1N NaOH and saturated NaCl before being dried over with Na2SO4. Concentration of organic solution gave the crude compound, which was purified on silica gel (100% EtOAc) to give the desired compound, which was treated with 1 equivalent of etherate HCL to form HCl salt for title compound. MS (APPI) m/z 394.4.

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washThe organic solution was washed with 1N NaOH and saturated NaCl
  4. dry with materialbefore being dried over with Na2SO4
  5. customConcentration of organic solution gave the crude compound, which
  6. customwas purified on silica gel (100% EtOAc)

출처 및 근거

ORD 기록
ord-6739cf9661714229a53e30ab143d85b7
출처 데이터셋
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07495111B2

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