Ammonia → HCID 178508172, 화합물

HRID 1992576

반응식

HRID 1992576 반응식
[C:1]1(S(Cl)(=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS(Cl)(=O)=O.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19](S(Cl)(=O)=O)=[CH:18][CH:17]=1.[NH3:27].[OH-].[NH4+:29].[C:30](=O)([O-])[O-].[NH4+:34].[NH4+:35].[C:36](=O)(O)[O-].[NH4+:40].P([O-])([O-])([O-])=O.[NH4+].[NH4+].[NH4+]>C(Cl)(Cl)Cl.ClCCl>[NH:27]1[C:2]2[C:3]3[N:35]=[CH:1][CH:6]=[CH:5][C:4]=3[N:34]=[C:17]([NH2:40])[C:16]=2[N:29]=[CH:30]1.[NH:27]1[C:26]2[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:34]=[C:2]([NH2:35])[C:1]=2[N:29]=[CH:36]1

참가 물질

12

반응물 8

HCID 222AmmoniaHCID 7369Benzenesulfonyl chlorideHCID 73974-Toluenesulfonyl chloride2회HCID 14013Ammonium BicarbonateHCID 14923Ammonium Hydroxide2회HCID 31297Methanesulfonyl chlorideHCID 159282Ammonium phosphate, tribasicHCID 517111Ammonium Carbonate

생성물 2

HCID 178508172HCID 178508172, 화합물HCID 178508191HCID 178508191, 화합물

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

In step (10) of Reaction Scheme I, a 1H-imidazo[4,5-c][1,5]naphthyridine-5N-oxide or 1H-imidazo[4,5-c]quinoline-5N-oxide of Formula XXIV is aminated to provide a 1H-imidazo[4,5-c][1,5]naphthyridin-4-amine or 1H-imidazo[4,5-c]quinolin-4-amine of Formula XXV. Step (10) involves the activation of an N-oxide of Formula XXIV by conversion to an ester and then reacting the ester with an aminating agent. Suitable activating agents include alkyl- or arylsulfonyl chlorides such as benzenesulfonyl chloride, methanesulfonyl chloride, or p-toluenesulfonyl chloride. Suitable aminating agents include ammonia, in the form of ammonium hydroxide, for example, and ammonium salts such as ammonium carbonate, ammonium bicarbonate, and ammonium phosphate. The reaction is conveniently carried out by adding ammonium hydroxide to a solution of the N-oxide of Formula XXIV in a suitable solvent such as dichloromethane or chloroform and then adding p-toluenesulfonyl chloride. The reaction can be carried out at ambient temperature. Under these reaction conditions, the N-phthalimide protecting group is removed to provide the 1H-imidazo[4,5-c][1,5]naphthyridin-4-amine or 1H-imidazo[4,5-c]quinolin-4-amine of Formula XXV or a pharmaceutically acceptable salt thereof, which can be isolated from the reaction mixture using conventional methods.

후처리

  1. customThe reaction
  2. customcan be carried out at ambient temperature
  3. customUnder these reaction conditions
  4. customthe N-phthalimide protecting group is removed

출처 및 근거

ORD 기록
ord-01a3e13e10e24917aa6a2f69b610fbe8
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07648997B2

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