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

HRID 863502노트

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HRID 863502 반응식
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]

참가 물질

9

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

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온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4f48ac3c43a34b48bef207f9d89b1cb1
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05721234

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