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 1172796ノート

反応式

HRID 1172796 の反応式
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

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-219cd7cd2f2d4d2da9d32a35c67a3d64
出典データセット
uspto-grants-2010_11
特許番号
US07834015B2

反応ノート

読み込み中…