Dichloromethane → 4-(6-Nitro-2,3-dioxo-1,2,3,4,7,8,9,10-octahydrobenzo[f]quinoxaline-9-ylcarbamoyl)-piperidine hydrochloride

HRID 863502ノート

反応式

HRID 863502 の反応式
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)(OC(C)(C)C)=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:29][CH:30]1[CH2:48][C:34]2[C:35]3[NH:36][C:37](=[O:47])[C:38](=[O:46])[NH:39][C:40]=3[CH:41]=[C:42]([N+:43]([O-:45])=[O:44])[C:33]=2[CH2:32][CH2:31]1.FC(F)(F)C(O)=O.C(Cl)[Cl:57]>O1CCCC1.CN(C)C=O.C(N(CC)CC)C>[ClH:57].[N+:43]([C:42]1[C:33]2[CH2:32][CH2:31][CH:30]([NH:29][C:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[O:16])[CH2:48][C:34]=2[C:35]2[NH:36][C:37](=[O:47])[C:38](=[O:46])[NH:39][C:40]=2[CH:41]=1)([O-:45])=[O:44]

参加物

9

反応物 5

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 196962049-Amino-6-nitro-1,4,7,8,9,10-hexahydro-benzo[f]quinoxaline-2,3-dione

生成物 1

HCID 196961494-(6-Nitro-2,3-dioxo-1,2,3,4,7,8,9,10-octahydrobenzo[f]quinoxaline-9-ylcarbamoyl)-piperidine hydrochloride

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

反応条件

温度
70 °C

実験手順

A mixture of N-Boc-piperidine-4-carboxylic acid (0.92 g, 4 mmol) and carbonyldiimidazole (0.65 g, 4 mmol) in 10 mL tetrahydrofuran was heated at reflux for 15 min. The mixture was added to the starting amine (Example 15, 0.6 g, 2 mmol) in 10 mL dimethylformamide and heated at 70° C. for 30 min. Triethylamine (0.4 g) was added and the mixture heated an additional 18 h. The solvent was evaporated and the yellow solid was washing with tetrahydrofuran, collected by filtration and dried to give 0.74 g. The solid was suspended in 50 mL methylene chloride, cooled in an icebath and treated with trifluoroacetic acid (1 g). After evaporating the solvent, the solid was washed with ether and acetone mixture and dried. Calc'd for C18H21N5O5.1.5HCl.H2O: C, 40.82; H, 4.57; N, 13.22; found-C, 40.35; H, 4.70; N, 12.91.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 15 min
  3. temperaturethe mixture heated an additional 18 h
  4. customThe solvent was evaporated
  5. washthe yellow solid was washing with tetrahydrofuran
  6. filtrationcollected by filtration
  7. customdried
  8. customto give 0.74 g
  9. temperaturecooled in an icebath
  10. customAfter evaporating the solvent
  11. washthe solid was washed with ether and acetone mixture
  12. customdried

出典と根拠

ORDレコード
ord-4f48ac3c43a34b48bef207f9d89b1cb1
出典データセット
uspto-grants-1998_02
特許番号
US05721234

反応ノート

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