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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
Notes
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Reaction equation

HRID 896343 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 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 ester
Yield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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:

Workup

  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)

Sources & evidence

ORD record
ord-549d3fc9d32d4af99b28508979c4d883
Source dataset
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06919331B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes