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Sodium Dithionite → (R)-tert-Butyl (1-(2-(1-ethyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazole-5-carbonyl)piperidin-3-yl)carbamate

HRID 2275015
Notes
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Reaction equation

HRID 2275015 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14](=[O:28])[C:15]2[CH:20]=[C:19]([N+:21]([O-])=O)[C:18]([NH:24][CH3:25])=[C:17]([O:26][CH3:27])[CH:16]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH2:30]([N:32]1[C:36]2=[N:37][CH:38]=[CH:39][CH:40]=[C:35]2[CH:34]=[C:33]1[CH:41]=O)[CH3:31].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)C.O.C(Cl)Cl>[C:1]([O:5][C:6](=[O:29])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([C:15]2[CH:16]=[C:17]([O:26][CH3:27])[C:18]3[N:24]([CH3:25])[C:41]([C:33]4[N:32]([CH2:30][CH3:31])[C:36]5=[N:37][CH:38]=[CH:39][CH:40]=[C:35]5[CH:34]=4)=[N:21][C:19]=3[CH:20]=2)=[O:28])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 24489Sodium DithioniteHCID 863401741-Ethyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehydeHCID 86340183(R)-tert-Butyl (1-(3-methoxy-4-(methylamino)-5-nitrobenzoyl)piperidin-3-yl)carbamate

Product 1

HCID 86340157(R)-tert-Butyl (1-(2-(1-ethyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazole-5-carbonyl)piperidin-3-yl)carbamateYield 75%

Reagents, catalysts & solvents

3
HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (R)-tert-butyl(1-(3-methoxy-4-(methylamino)-5-nitrobenzoyl)piperidin-3-yl)carbamate (4.5 g, 11.02 mmol) and 1-ethyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde (2.015 g, 11.57 mmol) in ethanol (100 mL) was added portionwise a solution of sodium dithionite (4.25 g, 20.75 mmol) in water (50 mL). The mixture was flushed with nitrogen then heated at 100° C. overnight (16 hours). The reaction mixture was concentrated under vacuum then diluted with DCM (150 ml) and water (150 ml). The organic layer was collected and the aqueous layer washed with DCM (3×100 ml). Organic layers were combined and back washed with water (3×150 ml), collected, dried with Na2SO4, filtered through a hydrophobic frit and concentrated under vacuum to yield 5.5 g of crude product as white solid. The crude product was dissolved in a minimum volume of DCM and purified using Biotage SP4 on a SNAP 100 g silica cartridge. The column was eluted with a gradient of 70-100% ethyl acetate in DCM for 10CV. Appropriate fractions were collected and concentrated in vacuo to afford the title compound as a white solid (4.40 g).

Workup

  1. customThe mixture was flushed with nitrogen
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. additionthen diluted with DCM (150 ml) and water (150 ml)
  4. customThe organic layer was collected
  5. washthe aqueous layer washed with DCM (3×100 ml)
  6. washback washed with water (3×150 ml)
  7. customcollected
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered through a hydrophobic frit
  10. concentrationconcentrated under vacuum
  11. customto yield 5.5 g of crude product as white solid
  12. custompurified
  13. washThe column was eluted with a gradient of 70-100% ethyl acetate in DCM for 10CV
  14. customAppropriate fractions were collected
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb1263847c5744319c25b200deb10a1b
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09127003B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes