Ammonia methanol → 8-amino-1-[3-(aminosulfonyl)phenyl]-1H-benzo[g]indazole-3-carboxamide

HRID 22983

반응식

HRID 22983 반응식
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([N:11]2[C:19]3[C:18]4[CH:20]=[C:21]([N+:24]([O-])=O)[CH:22]=[CH:23][C:17]=4[CH2:16][CH2:15][C:14]=3[C:13]([C:27]([O:29]CC)=O)=[N:12]2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[NH3:32].CO>>[NH2:24][C:21]1[CH:22]=[CH:23][C:17]2=[CH:16][CH:15]=[C:14]3[C:19]([N:11]([C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([NH2:1])(=[O:3])=[O:4])[CH:6]=4)[N:12]=[C:13]3[C:27]([NH2:32])=[O:29])=[C:18]2[CH:20]=1

참가 물질

3

반응물 2

HCID 21705897Ammonia methanolHCID 22592520Ethyl 1-[3-(aminosulfonyl)phenyl]-8-nitro-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate

생성물 1

HCID 225925238-amino-1-[3-(aminosulfonyl)phenyl]-1H-benzo[g]indazole-3-carboxamide

실험 절차

A sealed solution of ethyl 1-[3-(aminosulfonyl)phenyl]-8-nitro-4,5-dihydro-1H-benzo[g]indazole-3-carboxylat from step 1 (2.20 g, 4.98 mmol) in excess NH3/MeOH was heated at 110° C. for 10 h. The mixture was then concentrated to 10 mL, cooled to RT and the solid product collected by filtration. The solid was dissolved in HOAc, exposed to H2 (5 psi) at RT in the presence of Pd—C (5%) for 2 h. The mixture was filtered through celite pad, concentrated, taken into MeOH, filtered again through celite. The clear solution was concentrated, recrystallized in EtOH to give a grey solid (450 mg). Its structure was confirmed by 1H NMR and MS (382, M+1). C18H15N5O3S.H2O.(Et2O)0.2, Calc.: C: 54.51, H: 4.62, N: 16.91; Found, C: 54.79, H: 4.06, N: 16.72.

후처리

  1. concentrationThe mixture was then concentrated to 10 mL
  2. filtrationthe solid product collected by filtration
  3. dissolutionThe solid was dissolved in HOAc
  4. filtrationThe mixture was filtered through celite pad
  5. concentrationconcentrated
  6. filtrationfiltered again through celite
  7. concentrationThe clear solution was concentrated
  8. customrecrystallized in EtOH

출처 및 근거

ORD 기록
ord-aadaed8f897b48b8936e8f9333abddf7
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849653B2

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