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

HRID 246734
Notes
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Reaction equation

HRID 246734 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[N:6]=[C:5]2[C:12]1[N:17]=[C:16]2[C:18]([C:40]([O:42][CH3:43])=[O:41])=[CH:19][N:20]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:15]2=[N:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:51][CH2:52][CH2:53][C:54]([CH3:59])([N+:56]([O-:58])=[O:57])[CH3:55].O>CN(C=O)C>[CH3:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([O:1][CH2:51][CH2:52][CH2:53][C:54]([CH3:59])([N+:56]([O-:58])=[O:57])[CH3:55])=[CH:10][CH:9]=2)[C:5]([C:12]2[N:17]=[C:16]3[C:18]([C:40]([O:42][CH3:43])=[O:41])=[CH:19][N:20]([C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:15]3=[N:14][CH:13]=2)=[N:6]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 553015211-Chloro-4-methyl-4-nitropentaneHCID 71280393methyl 2-(5-hydroxy-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate

Product 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
Yield 66.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 2-(5-hydroxy-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (2.2 g, 3.9 mmol) in DMF (25 mL) was added K2CO3 (1.8 g, 12.8 mmol) and 1-chloro-4-methyl-4-nitropentane (1.0 g, 5.9 mmol), after the addition, the reaction mixture was heated to 100° C. with stirring for 4 hours. The reaction mixture was cooled to room temperature, H2O (25 mL) was added and product extracted with EtOAc (100 mL). The organic layer was washed with H2O (100 mL) and brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure to give methyl 2-(1-methyl-5-(4-methyl-4-nitropentyloxy)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (1.8 g, 66.7%) as yellow solid. LCMS: (M+H)+=695.

Workup

  1. additionafter the addition
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionproduct extracted with EtOAc (100 mL)
  4. washThe organic layer was washed with H2O (100 mL) and brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7dfd75488c054b608237d6830793c8dd
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