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

HRID 2275011Notes

Reaction equation

HRID 2275011 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:46]2[CH:45]=[CH:44][N:43]=[CH:42][C:41]=2[CH:40]=[C:39]1[CH:47]=O)[CH3:37].CO>O.C(O)C>[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:46]5[CH:45]=[CH:44][N:43]=[CH:42][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

7

Reactant 4

HCID 887MethanolHCID 24489Sodium DithioniteHCID 900279831-ethyl-1H-pyrrolo[3,2-c]pyridine-2-carbaldehydeHCID 118181215tert-Butyl(1(4-(methylamino)-3-nitrobenzoyl)piperidin-3-yl)carbamate

Product 1

HCID 118178617tert-Butyl(1-(2-(1-ethyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-1-methyl-1H-benzo[d]imidazole-5-carbonyl)piperidin-3-yl)carbamateYield 40%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Sodium hydrosulfite (277.4 mg, 1.275 mmol) dissolved in water (1.5 mL) was added to a stirred solution of tert-butyl(1-(4-(methylamino)-3-nitrobenzoyl)piperidin-3-yl)carbamate (143.2 mg, 0.378 mmol) and 1-ethyl-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde (67.6 mg, 0.388 mmol) in ethanol (3.5 mL) at room temperature in a 5 ml microwave vial. The reaction mixture was then heated in a microwave for 5 hr at 100° C. Methanol was added to the reaction mixture and dried using Na2SO4. The reaction mixture was then filtered under gravity through a hydrophobic frit and the eluent collected and concentrated under vacuum. The crude product was dissolved in a minimum volume of DCM and purified using SP4 on a 25 g SNAP silica cartridge. The cartridge was eluted using a gradient of 0-100% 20% methanol in DCM/DCM. Appropriate fractions were collected and concentrated under vacuum to give the title compound as a yellow oil (76 mg).

Workup

  1. customdried
  2. filtrationThe reaction mixture was then filtered under gravity through a hydrophobic frit
  3. customthe eluent collected
  4. concentrationconcentrated under vacuum
  5. dissolutionThe crude product was dissolved in a minimum volume of DCM
  6. custompurified
  7. washThe cartridge was eluted
  8. customAppropriate fractions were collected
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e979d810b2944e4e965f9109abc4670e
Source dataset
uspto-grants-2015_09
Patent number
US09127003B2

Reaction notes

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