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Hydrochloric Acid → 9-Acetyl-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

HRID 532933
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HRID 532933 반응식
I[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]1[C:16](=[O:17])[CH2:15][NH:14][C:13](=[O:18])[CH:12]=[C:7]12.C([Sn](CCCC)(CCCC)[C:24]([O:26]CC)=[CH2:25])CCC.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1.C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:24]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]1[C:16](=[O:17])[CH2:15][NH:14][C:13](=[O:18])[CH:12]=[C:7]12)(=[O:26])[CH3:25]
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참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 867113799-Iodo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

생성물 1

HCID 867113789-Acetyl-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione수율 69.6%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 8028Tetrahydrofuran용매
HCID 312751,4-Dioxane용매

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온도
140 °C

실험 절차

100-1. A mixture of 9-iodo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione (150 mg, 0.42 mmol), tributyl(1-ethoxyvinyl)stannane (153 mg, 0.42 mmol) and Pd(PPh3)4 (49 mg, 0.04 mmol) in dioxane (3 mL) was heated to 140° C. for 2 h in a microwave reactor. The mixture was then concentrated in vacuo and the residue obtained was purified by flash chromatography (SiO2, heptane to AcOEt to AcOEt/MeOH 85:15) afforded the compound obtained was taken up in THF (20 mL) and treated with a 2M aqueous solution of HCl (0.68 mL, 1.36 mmol). The solution was stirred at RT for 1 h and then concentrated in vacuo. The residue obtained was taken up in a saturated aq. solution of NaHCO3 and extracted with DCM. The combined org. layers were then dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (79 mg). UPLC-MS: MS 271.2 (M+H+); UPLC rt 0.59 min.

후처리

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue obtained
  3. customwas purified by flash chromatography (SiO2, heptane to AcOEt to AcOEt/MeOH 85:15)
  4. customafforded the compound
  5. customobtained
  6. concentrationconcentrated in vacuo
  7. customThe residue obtained
  8. extractionextracted with DCM
  9. dry with materiallayers were then dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-dc59429b62d743fb90d6a8a1be74f1a0
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08853203B2

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