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Hydrochloric Acid → [2-[3-(2-fluoro-ethoxyimino)-2-oxo-2,3-dihydro-pyrrolo[2,3-b]pyridin-1-ylmethyl]-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester

HRID 896343
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HRID 896343 반응식
[F:1][CH2:2][CH2:3][O:4][N:5]=[C:6]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:15].C([O-])([O-])=O.[Cs+].[Cs+].[C:22]([O:26][C:27](=[O:46])[NH:28][CH2:29][C:30]1[CH:45]=[CH:44][C:33]2[N:34]([CH2:39][CH2:40][CH:41]([CH3:43])[CH3:42])[C:35]([CH2:37]Cl)=[N:36][C:32]=2[CH:31]=1)([CH3:25])([CH3:24])[CH3:23].Cl>CN(C=O)C>[C:22]([O:26][C:27](=[O:46])[NH:28][CH2:29][C:30]1[CH:45]=[CH:44][C:33]2[N:34]([CH2:39][CH2:40][CH:41]([CH3:42])[CH3:43])[C:35]([CH2:37][N:8]3[C:9]4=[N:10][CH:11]=[CH:12][CH:13]=[C:14]4[C:6](=[N:5][O:4][CH2:3][CH2:2][F:1])[C:7]3=[O:15])=[N:36][C:32]=2[CH:31]=1)([CH3:23])([CH3:25])[CH3:24]
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 59561810HCID 59561810, 화합물HCID 1363860121H-Pyrrolo[2,3-b]pyridine-2,3-dione 3-[O-(2-fluoro-ethyl)-oxime]

생성물 1

HCID 86590116[2-[3-(2-fluoro-ethoxyimino)-2-oxo-2,3-dihydro-pyrrolo[2,3-b]pyridin-1-ylmethyl]-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester수율 72%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 1H-pyrrolo[2,3-b]pyridine-2,3-dione 3-[O-(2-fluoro-ethyl)-oxime] (23 mg, 0.11 mmol) in DMF (1.6 mL) was added Cs2CO3 (108 mg, 0.33 mmol). After stirring for 20 minutes, [2-chloromethyl-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester; HCl salt (44 mg, 0.11 mmol) was added and the resulting mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate and the combined organic fractions washed with water, brine, dried over MgSO4 and evaporated. The residue was purified by flash chromatography (eluant 1%, 5% MeOH in CH2Cl2) to give [2-[3-(2-fluoro-ethoxyimino)-2-oxo-2,3-dihydro-pyrrolo[2,3-b]pyridin-1-ylmethyl]-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester (53 mg, 72%) as an off-white solid:

후처리

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between ethyl acetate and water
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washthe combined organic fractions washed with water, brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue was purified by flash chromatography (eluant 1%, 5% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-549d3fc9d32d4af99b28508979c4d883
출처 데이터셋
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06919331B2

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