Cesium carbonate → N-(1-((6-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)pyridin-2-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79408노트

반응식

HRID 79408 반응식
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[N:26]=2)[N:4]=1)[CH3:2].CS(O[CH2:37][CH:38]1[CH2:42][O:41][C:40]([CH3:44])([CH3:43])[O:39]1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CC(N(C)C)=O>[CH3:43][C:40]1([CH3:44])[O:39][CH:38]([CH2:37][O:31][C:27]2[N:26]=[C:25]([CH2:24][N:5]3[C:6]4[C:11](=[C:10]([NH:12][C:13]([C:15]5[N:19]6[CH:20]=[CH:21][CH:22]=[CH:23][C:18]6=[N:17][CH:16]=5)=[O:14])[CH:9]=[CH:8][CH:7]=4)[C:3]([CH2:1][CH3:2])=[N:4]3)[CH:30]=[CH:29][CH:28]=2)[CH2:42][O:41]1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 15570840(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonateHCID 178437935HCID 178437935, 화합물

생성물 1

HCID 67259775N-(1-((6-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)pyridin-2-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide수율 58.4%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

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온도
90 °C

실험 절차

To N-(3-ethyl-1-((6-hydroxypyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (17, Step A) (16 mg, 0.039 mmol) in DMA (2 mL) was added (2,2-dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate (8.2 mg, 0.039 mmol) and Cs2CO3 (25 mg, 0.078 mmol). The reaction vial was sealed and the mixture was heated at 90° C. for 6 hours. The DMA was removed under reduced pressure. The residue was diluted with EtOAc (20 mL). The organic solution was washed with saturated NaHCO3 aqueous solution and brine, and then concentrated under reduced pressure. Silica gel chromatography (DCM/MeOH 10:0.5) gave the product (12 mg).

후처리

  1. customThe reaction vial was sealed
  2. customThe DMA was removed under reduced pressure
  3. additionThe residue was diluted with EtOAc (20 mL)
  4. washThe organic solution was washed with saturated NaHCO3 aqueous solution and brine
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-201f28a51ada4d539f8ea3f962ea3de5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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