Triethylamine → 9-Iodo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

HRID 532875ノート

反応式

HRID 532875 の反応式
[I:1][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])[CH2:12][CH:7]12.[Cl-].C(CC1C2C(=C(I)C=CC=2)CCN1C(=O)C[NH3+])(O)=O.CCN(CC)CC.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CN(C=O)C.CCOC(C)=O.C([O-])(O)=O.[Na+].CO>[I:1][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

参加物

9

反応物 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 867113252-(1-(carboxymethyl)-5-iodo-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanaminium chlorideHCID 86711327HCID 86711327、化合物

生成物 1

HCID 867113799-Iodo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

9-iodo-1,3,4,7,8,12b-hexahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione. A suspension of 2-(1-(carboxymethyl)-5-iodo-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanaminium chloride (46.1 g, 112 mmol) and Et3N (95 mL, 682 mmol) in dry DMF (1.1 L) was treated with a solution of T3P in DMF (98 mL, 169 mmol)—exothermic. The mixture was stirred at RT overnight. The mixture was then concentrated in vacuo and the residue obtained was taken up in AcOEt and diluted with an saturated aq. solution of NaHCO3. The aqueous phase was extracted with AcOEt and the combined org. layers were then washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give a brown solid. The crude product obtained was suspended in MeOH and filtered. The filter cake was washed with MeOH and DCM, and then dried in vacuo to give the title compound (12.4 g) as a beige powder that was used as it is in the next step. UPLC-MS: MS 357.1 (M+H+); UPLC rt 0.73 min.

後処理

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue obtained
  3. extractionThe aqueous phase was extracted with AcOEt
  4. washlayers were then washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a brown solid
  9. customThe crude product obtained
  10. filtrationfiltered
  11. washThe filter cake was washed with MeOH and DCM
  12. customdried in vacuo

出典と根拠

ORDレコード
ord-32cdb13432e14207bfb7b09a8f93f346
出典データセット
uspto-grants-2014_10
特許番号
US08853203B2

反応ノート

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