Dimethylamine → Topotecan

HRID 1084459

反応式

HRID 1084459 の反応式
[CH3:1][CH2:2][C@@:3]1([OH:27])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[C:23]1[N:22]=[C:21]2[C:16]([CH:17]=[C:18]([OH:26])[CH:19]=[CH:20]2)=[CH:15][C:14]=1[CH2:13]3)=[O:11].C(O)C.[CH2:31]=O.[CH3:33][NH:34][CH3:35]>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>[CH3:1][CH2:2][C@@:3]1([OH:27])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[C:23]1[N:22]=[C:21]2[C:16](=[CH:15][C:14]=1[CH2:13]3)[C:17]([CH2:33][N:34]([CH3:31])[CH3:35])=[C:18]([OH:26])[CH:19]=[CH:20]2)=[O:11]

参加物

6

反応物 4

HCID 674DimethylamineHCID 702EthanolHCID 712FormaldehydeHCID 97226Hydroxycamptothecin

生成物 1

HCID 60700Topotecan

試薬・触媒・溶媒 1

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester溶媒

実験手順

A mixture of 10-hydroxycamptothecin (728 mg 2.0 mmol), prepared as described in Example 2, in glacial acetic (50 mL), ethanol (20 mL), 37% aqueous formaldehyde (3 mL) and 40% aqueous dimethylamine (3 mL) was stirred at room temperature for 20 h. The solvents were removed under reduced pressure; the residue was heated at 50° under high vacuum for 2 h and triturated with isopropanol (10 mL) to precipitate the title compound (561 mg, 64%) as a yellow solid. FAB mass spectrum: m/e 422 (MH+). 1H NMR (CDCl3 /CD3OD) δ1.0 (t, 3), 1.9 (m, 2), 2.5 (s, 6), 4.3 (s, 2), 5.2 (s, 2), 5.4 (q, 2), 7.6 (s, 1), 7.7 (q, 2), 8.5 (s, 1).

後処理

  1. customprepared
  2. customThe solvents were removed under reduced pressure
  3. temperaturethe residue was heated at 50° under high vacuum for 2 h
  4. customtriturated with isopropanol (10 mL)
  5. customto precipitate the title compound (561 mg, 64%) as a yellow solid

出典と根拠

ORDレコード
ord-a452c7c3aea64705b2836406f397f1a8
出典データセット
uspto-grants-1991_04
特許番号
US05004758

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