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Potassium Carbonate → N-tert-butyl-2-(5-(difluoromethoxy)-1-(4-methyl-4-nitropentyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

HRID 246752
Notes
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Reaction equation

HRID 246752 reaction equation
[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH:27]([F:29])[F:28])[CH:24]=4)[NH:19][N:18]=3)=[CH:15][N:16]=[C:11]2[N:10]([C:30]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Cl[CH2:56][CH2:57][CH2:58][C:59]([CH3:64])([N+:61]([O-:63])=[O:62])[CH3:60]>CN(C=O)C>[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH:27]([F:29])[F:28])[CH:24]=4)[N:19]([CH2:56][CH2:57][CH2:58][C:59]([CH3:64])([N+:61]([O-:63])=[O:62])[CH3:60])[N:18]=3)=[CH:15][N:16]=[C:11]2[N:10]([C:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 553015211-Chloro-4-methyl-4-nitropentaneHCID 71279313N-tert-butyl-2-(5-(difluoromethoxy)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Product 1

HCID 71280547N-tert-butyl-2-(5-(difluoromethoxy)-1-(4-methyl-4-nitropentyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamideYield 74%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-tert-butyl-2-(5-(difluoromethoxy)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (208 mg, 0.35 mmol) in DMF (15 mL) was added K2CO3 (193 mg, 1.4 mmol) and 1-chloro-4-methyl-4-nitropentane (100 mg, 0.59 mmol), after the addition, the reaction mixture was heated to 100° C. with stirring for 4 hours. Then, the mixture was quenched with H2O (25 mL) and product extracted with EtOAc (50 mL). The organic layer was washed with H2O (100 mL), brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure to give N-tert-butyl-2-(5-(difluoromethoxy)-1-(4-methyl-4-nitropentyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (200 mg, 69%) as yellow solid, material used in the next step without further purification. LCMS: (M+H)+=772; (M+Na)+=794.0.

Workup

  1. additionafter the addition
  2. customThen, the mixture was quenched with H2O (25 mL) and product
  3. extractionextracted with EtOAc (50 mL)
  4. washThe organic layer was washed with H2O (100 mL), brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2e4f3a71d1b14b5fb21d3d4492c64337
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658646B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes