Sodium Bicarbonate → tert-Butyl 4-[(4-{3-[[(4-chloro-1H-pyrrol-2-yl)carbonyl](2,4-dimethoxybenzyl)amino]prop-1-yn-1-yl}pyridin-2-yl)carbonyl]-1,4-diazepane-1-carboxylate

HRID 1172796노트

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HRID 1172796 반응식
FC(F)(F)C([O-])=O.ClC1C=C2C(=O)NC=C(CC3C=CC(F)=C(C=3)C(N3CCC[NH2+]CC3)=O)N2C=1.[Cl:36][C:37]1[CH:38]=[C:39]([C:42]([O:44]N2C(=O)CCC2=O)=O)[NH:40][CH:41]=1.[CH3:52][O:53][C:54]1[CH:86]=[C:85]([O:87][CH3:88])[CH:84]=[CH:83][C:55]=1[CH2:56][NH:57][CH2:58][C:59]#[C:60][C:61]1[CH:66]=[CH:65][N:64]=[C:63]([C:67]([N:69]2[CH2:75][CH2:74][CH2:73][N:72]([C:76]([O:78][C:79]([CH3:82])([CH3:81])[CH3:80])=[O:77])[CH2:71][CH2:70]2)=[O:68])[CH:62]=1.C([O-])(O)=O.[Na+]>CC#N.O>[Cl:36][C:37]1[CH:38]=[C:39]([C:42]([N:57]([CH2:56][C:55]2[CH:83]=[CH:84][C:85]([O:87][CH3:88])=[CH:86][C:54]=2[O:53][CH3:52])[CH2:58][C:59]#[C:60][C:61]2[CH:66]=[CH:65][N:64]=[C:63]([C:67]([N:69]3[CH2:75][CH2:74][CH2:73][N:72]([C:76]([O:78][C:79]([CH3:82])([CH3:80])[CH3:81])=[O:77])[CH2:71][CH2:70]3)=[O:68])[CH:62]=2)=[O:44])[NH:40][CH:41]=1

참가 물질

7

반응물 4

HCID 516892Sodium BicarbonateHCID 686892094-{5-[(7-Chloro-1-oxo-1,2-dihydropyrrolo[1,2-a]pyrazin-4-yl)methyl]-2-fluorobenzoyl}-1,4-diazepan-1-ium trifluoroacetateHCID 866334231-{[(4-Chloro-1H-pyrrol-2-yl)carbonyl]oxy}pyrrolidine-2,5-dioneHCID 86633427tert-Butyl 4-[(4-{3-[(2,4-dimethoxybenzyl)amino]prop-1-yn-1-yl}pyridin-2-yl)carbonyl]-1,4-diazepane-1-carboxylate

생성물 1

HCID 86633426tert-Butyl 4-[(4-{3-[[(4-chloro-1H-pyrrol-2-yl)carbonyl](2,4-dimethoxybenzyl)amino]prop-1-yn-1-yl}pyridin-2-yl)carbonyl]-1,4-diazepane-1-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A solution of Example 6, F1 (2 eq), I2 (1 eq) and NaHCO3 (2.5 eq) in a mixture of CH3CN and H2O (20:1) was heated at reflux for 12 hrs and then the MeCN was removed under reduced pressure. The resulting residue was partitioned between DCM and water. The organic phase was washed with brine, dried (Na2SO4), filtered, concentrated under reduced pressure. The resulting brown oil was purified by Biotage system eluting with EtOAc/petroleum ether to obtain the desired compound. MS (ES) C33H38ClN5O6 requires: 635, found: 636 (M+H)+.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 12 hrs
  3. customthe MeCN was removed under reduced pressure
  4. customThe resulting residue was partitioned between DCM and water
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting brown oil was purified by Biotage system
  10. washeluting with EtOAc/petroleum ether

출처 및 근거

ORD 기록
ord-219cd7cd2f2d4d2da9d32a35c67a3d64
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834015B2

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