Cesium carbonate → (S)-tert-butyl 3-(6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yloxy)pyrrolidine-1-carboxylate

HRID 79304노트

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HRID 79304 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[C@@H:37]1[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38]1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CC(N(C)C)=O>[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[N:26]=[C:27]([O:31][C@H:41]3[CH2:37][CH2:38][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:40]3)[CH:28]=[CH:29][CH:30]=2)[N:4]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 10934372Tert-butyl (3R)-3-(methanesulfonyloxy)pyrrolidine-1-carboxylateHCID 178437935HCID 178437935, 화합물

생성물 1

HCID 70814880(S)-tert-butyl 3-(6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yloxy)pyrrolidine-1-carboxylate수율 50.6%

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 (21 mg, 0.051 mmol) in DMA (2 mL) was added (R)-tert-butyl 3-(methylsulfonyloxy)pyrrolidine-1-carboxylate (20 mg, 0.076 mmol) and Cs2CO3 (33 mg, 0.10 mmol). The reaction vial was sealed, and the reaction was heated to 90° C. and stirred for 6 hours. DMA was removed under reduce pressure. The residue was diluted with EtOAc (20 mL), washed with saturated NaHCO3 aqueous solution (5 mL) and brine (5 mL), and concentrated. Silica gel chromatography of the crude material (DCM/MeOH 10:0.5) provided the desired product (15 mg).

후처리

  1. customThe reaction vial was sealed
  2. customDMA was removed
  3. additionThe residue was diluted with EtOAc (20 mL)
  4. washwashed with saturated NaHCO3 aqueous solution (5 mL) and brine (5 mL)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1885a0e738a94714aea0ffd29319f71a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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