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

HRID 532882ノート

反応式

HRID 532882 の反応式
[Br: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-].BrC1C=CC=C2C=1CCN(C(=O)C[NH3+])C2CC(O)=O.C(N(CC)CC)C.Cl>C(Cl)Cl.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.CCOC(C)=O>[Br: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

8

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 867113302-(5-bromo-1-(carboxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanaminium chlorideHCID 867113339-Bromo-1,3,4,7,8,12b-hexahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

生成物 1

HCID 867113289-Bromo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒HCID 111923Propylphosphonic anhydride溶媒

実験手順

9-bromo-1,3,4,7,8,12b-hexahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione. To a stirred solution of 2-(5-bromo-1-(carboxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanaminium chloride (88 g, 242 mmol) and triethylamine (169 mL, 1210 mmol) in DCM (960 mL), T3P (212 mL, 363 mmol, 50% m/m in AcOEt) was added slowly (exotherm) and the suspension was stirred at rt for 1 h. The solvent was reduced to a small amount under reduced pressure and the thick suspension was treated with 2N aqueous HCl (500 mL). The white suspension was stirred at RT for 15 min and the solid was filtered off. The solid was again treated with 2N aqueous HCl (300 mL), stirred for 10 min and filtered of. The slightly yellow solid was washed with water (1×) and with diethyl ether (2×). The resulting solid was dried at 50° C. under high vacuo overnight to yield the title compound as beige solid (71 g). UPLC-MS: MS 309.1/311.1 (M+H+); UPLC rt 0.72 min.

後処理

  1. stirringThe white suspension was stirred at RT for 15 min
  2. filtrationthe solid was filtered off
  3. additionThe solid was again treated with 2N aqueous HCl (300 mL)
  4. stirringstirred for 10 min
  5. filtrationfiltered of
  6. washThe slightly yellow solid was washed with water (1×) and with diethyl ether (2×)
  7. customThe resulting solid was dried at 50° C. under high vacuo overnight

出典と根拠

ORDレコード
ord-1c779dbee40e42ee86bc0970714ff10d
出典データセット
uspto-grants-2014_10
特許番号
US08853203B2

反応ノート

読み込み中…