Thionyl Chloride → N-(3-ethyl-1-((6-methoxypyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79298

반응식

HRID 79298 반응식
[N:1]1[CH:2]=[C:3]([C:10]([OH:12])=O)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.S(Cl)(Cl)=O.ClCCCl.C1COCC1.[CH2:26]([C:28]1[C:36]2[C:35]([NH2:37])=[CH:34][CH:33]=[CH:32][C:31]=2[N:30]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([O:45][CH3:46])[N:40]=2)[N:29]=1)[CH3:27]>C(Cl)Cl>[CH2:26]([C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][C:35]=2[NH:37][C:10]([C:3]2[N:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]3=[N:1][CH:2]=2)=[O:12])[N:30]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([O:45][CH3:46])[N:40]=2)[N:29]=1)[CH3:27]

참가 물질

6

반응물 4

HCID 24386Thionyl ChlorideHCID 73142Imidazo(1,2-a)pyridine-3-carboxylic acidHCID 21493386Dce thfHCID 672592283-ethyl-1-((6-methoxypyridin-2-yl)methyl)-1H-indazol-4-amine

생성물 1

HCID 67259608N-(3-ethyl-1-((6-methoxypyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide수율 70.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
70 °C

실험 절차

To imidazo[1,2-a]pyridine-3-carboxylic acid (194 mg, 1.20 mmol) in DCM (5 mL) was added thionyl chloride (2 mL). The reaction mixture was stirred for 2 hours and concentrated to give crude acylchloride HCl salt, to which DCE/THF (2 mL/2 mL) and 3-ethyl-1-((6-methoxypyridin-2-yl)methyl)-1H-indazol-4-amine (211 mg, 0.747 mmol) was added. The reaction mixture was heated to 70° C. and stirred for 1 hour. The reaction mixture was diluted with DCM (20 mL) and washed with saturated NaHCO3 aqueous solution. The organic solution was dried over Na2SO4, filtered and concentrated. Silica gel chromatography (DCM/MeOH 10:1) provided the desired product (226 mg). MS (ES+APCI) m/z=427 (M+H).

후처리

  1. concentrationconcentrated
  2. customto give crude acylchloride HCl salt
  3. stirringstirred for 1 hour
  4. washwashed with saturated NaHCO3 aqueous solution
  5. dry with materialThe organic solution was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c00b4facc8a94ea88374eda9c0943ec1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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