methyl 2-(1-methyl-5-(4-methyl-4-nitropentyloxy)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate → methyl 2-(5-(4-amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate

HRID 246735Notes

Reaction equation

HRID 246735 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:20])([N+:17]([O-])=O)[CH3:16])=[CH:8][CH:9]=2)[C:4]([C:21]2[N:26]=[C:25]3[C:27]([C:49]([O:51][CH3:52])=[O:50])=[CH:28][N:29]([C:30]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:24]3=[N:23][CH:22]=2)=[N:3]1>CO.[Pd]>[NH2:17][C:15]([CH3:20])([CH3:16])[CH2:14][CH2:13][CH2:12][O:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[N:3]=[C:4]2[C:21]1[N:26]=[C:25]2[C:27]([C:49]([O:51][CH3:52])=[O:50])=[CH:28][N:29]([C:30]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:24]2=[N:23][CH:22]=1

Participants

4

Reactant 1

HCID 71280089methyl 2-(1-methyl-5-(4-methyl-4-nitropentyloxy)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate

Product 1

HCID 71279592methyl 2-(5-(4-amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylateYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 2-(1-methyl-5-(4-methyl-4-nitropentyloxy)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (500 mg, 0.72 mmol) in CH3OH (15 mL) was added Pd/C (0.1 g, cat.) and HCO2NH4 (226 mg, 3.6 mmol), after the addition, the reaction mixture was heated to 80° C. with stirring for 0.5 hour, then the mixture was filtered and filtrate evaporated, the residue was partitioned between H2O (25 mL) and EtOAc (100 mL). The organic layer was washed with H2O (100 mL), brine (100 mL) dried over Na2SO4, filtered and concentrated under reduced pressure to give methyl 2-(5-(4-amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (400 mg, 85%) as yellow solid. LCMS: (M+H)+=665.

Workup

  1. additionafter the addition
  2. filtrationthe mixture was filtered
  3. customfiltrate evaporated
  4. customthe residue was partitioned between H2O (25 mL) and EtOAc (100 mL)
  5. washThe organic layer was washed with H2O (100 mL), brine (100 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d22baa3ea4884fbf99038d15c903b600
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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