O-Phenylenediamine → HCID 68671013, 화합물

HRID 2047365노트

반응식

HRID 2047365 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[CH2:13][CH2:12]2)=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.CN(C)CCCN=C=NCC.O.O[N:36]1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[N:38]=N1.C1(N)C=CC=CC=1N>CN(C=O)C.CN(C)C1C=CN=CC=1>[NH2:36][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=1[NH:38][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]([CH3:21])[CH3:20])[CH2:13][CH2:12]2)[CH:9]=[CH:10][C:2]=1[Cl:1]

참가 물질

7

반응물 4

HCID 7243O-PhenylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 686700692-Chloro-5-[4-(2-dimethylaminoethyl)-piperazin-1-yl]-benzoic acid

생성물 1

HCID 68671013HCID 68671013, 화합물수율 58.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-chloro-5-[4-(2-dimethylaminoethyl)-piperazin-1-yl]-benzoic acid (0.40 g, 1.29 mmol) in dry DMF (5 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (0.25 g, 1.29 mmol), followed by 1-hydroxybenzotriazole hydrate (1-HOBt) (0.11 g, 0.77 mmol) and dimethyl-pyridin-4-yl-amine (DMAP) (0.08 g, 0.64 mmol). After 3 h stirring at room temperature, 1,2-phenylenediamine (0.21 g, 1.93 mmol) was added, and the resulting mixture was stirred at room temperature overnight. The solution was evaporated under reduced pressure, then diluted with dichlomethane (20 mL) and washed with saturated Na2CO3 solution (2×5 mL). The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The resulting solid was purified by flash chromatography (eluent:dichloromethane:MeOH:NH3 in MeOH (2M)/9:0.5:0.5) to obtain 0.18 g (35%) of the title compound.

후처리

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe solution was evaporated under reduced pressure
  3. additiondiluted with dichlomethane (20 mL)
  4. washwashed with saturated Na2CO3 solution (2×5 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe resulting solid was purified by flash chromatography (eluent:dichloromethane:MeOH:NH3 in MeOH (2M)/9:0.5:0.5)

출처 및 근거

ORD 기록
ord-5cc06559e25b4b6698c946b450a9a111
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592463B2

반응 노트

불러오는 중…