1,2-Dichloroethane → 4-[6-amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-N-(2-diethylamino-ethyl)-benzamide

HRID 1766746노트

반응식

HRID 1766746 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)=[CH:4][C:3]=1[O:17][CH2:18][C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH2:41]([N:43]([CH2:47][CH3:48])[CH2:44][CH2:45][NH2:46])[CH3:42]>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([NH:46][CH2:45][CH2:44][N:43]([CH2:47][CH3:48])[CH2:41][CH3:42])=[O:14])=[CH:15][CH:16]=2)=[CH:4][C:3]=1[O:17][CH2:18][C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26]

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 60993N,N-DiethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 103181294-[6-Amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-benzoic acid

생성물 1

HCID 104355394-[6-amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-N-(2-diethylamino-ethyl)-benzamide수율 72%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-[6-amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-benzoic acid (50 mg, 0.13 mmol), HOBT (21 mg, 0.156 mmol), and EDC (30 mg, 0.156 mmol) in DMF (2 mL) was added N,N-diethylethylenediamine (0.022 mL, 0.156 mmol). The reaction was stirred at room temperature for 24 hr, then diluted with EtOAc, and partitioned with H2O. The organic was separated and the aqueous was extracted with EtOAc. The organic layers were combined, washed with saturated NaHCO3, and concentrated to dryness under vacuum. The material was purified using column chromatography (silica gel, 99:1 to 95:5 CH2Cl2/MeOH) to give 4-[6-amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-N-(2-diethylamino-ethyl)-benzamide (45 mg, 72% yield) as a white solid.

후처리

  1. custompartitioned with H2O
  2. customThe organic was separated
  3. extractionthe aqueous was extracted with EtOAc
  4. washwashed with saturated NaHCO3
  5. concentrationconcentrated to dryness under vacuum
  6. customThe material was purified

출처 및 근거

ORD 기록
ord-5dc3c46ee3cc485faeab0b0d6d77871d
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07230098B2

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