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

HRID 2275018Notes

Reaction equation

HRID 2275018 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[C:9]([O:13][C:14](=[O:35])[NH:15][CH:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:22](=[O:34])[C:23]2[CH:28]=[CH:27][C:26]([NH:29][CH3:30])=[C:25]([N+:31]([O-])=O)[CH:24]=2)[CH2:17]1)([CH3:12])([CH3:11])[CH3:10].[CH2:36]([N:38]1[C:42]2=[N:43][CH:44]=[CH:45][CH:46]=[C:41]2[CH:40]=[C:39]1[CH:47]=O)[CH3:37]>O.C(O)C.C(Cl)Cl.[O-]S([O-])(=O)=O.[Na+].[Na+]>[C:9]([O:13][C:14](=[O:35])[NH:15][CH:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:22]([C:23]2[CH:28]=[CH:27][C:26]3[N:29]([CH3:30])[C:47]([C:39]4[N:38]([CH2:36][CH3:37])[C:42]5=[N:43][CH:44]=[CH:45][CH:46]=[C:41]5[CH:40]=4)=[N:31][C:25]=3[CH:24]=2)=[O:34])[CH2:17]1)([CH3:12])([CH3:10])[CH3:11]

Participants

8

Reactant 3

HCID 24489Sodium DithioniteHCID 863401741-Ethyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehydeHCID 118181215tert-Butyl(1(4-(methylamino)-3-nitrobenzoyl)piperidin-3-yl)carbamate

Product 1

HCID 118178625tert-Butyl(1-(2-(1-ethyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-1-methyl-1H-benzo[d]imidazole-5-carbonyl)piperidin-3-yl)carbamateYield 54%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 24436Sodium SulfateSolvent

Conditions

Temperature
100 °C

Procedure

Sodium hydrosulfite (235 mg, 1.150 mmol) dissolved in water (1.500 mL) was added to a solution of tert-butyl(1-(4-(methylamino)-3-nitrobenzoyl)piperidin-3-yl)carbamate (145 mg, 0.383 mmol) and 1-ethyl-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde (66.7 mg, 0.383 mmol) in ethanol (3 mL) at RT under nitrogen. The reaction mixture was heated to 100° C. in a microwave for 5 h. The reaction mixture was diluted with DCM (20 mL), Na2SO4 was added and the resultant suspension filtered and concentrated in vacuo to yield the crude product as a yellow oil. The crude product was purified by Biotage SP4 on a SNAP 25 g silica cartridge using a gradient of 0% (20% MeOH/DCM)/DCM→100% (20% MeOH/DCM)/DCM. Appropriate fractions were combined and evaporated under vacuum to give the title compound as a yellow solid (104 mg).

Workup

  1. additionwas added
  2. filtrationthe resultant suspension filtered
  3. concentrationconcentrated in vacuo
  4. customto yield the crude product as a yellow oil
  5. customThe crude product was purified by Biotage SP4 on a SNAP 25 g silica cartridge
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-7734909c2a2142b5b810cd45859a793c
Source dataset
uspto-grants-2015_09
Patent number
US09127003B2

Reaction notes

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