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Potassium Hydroxide → 2-(5-(4-Amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid

HRID 246736
Notes
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Reaction equation

HRID 246736 reaction equation
[NH2:1][C:2]([CH3:50])([CH3:49])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[N:11]=[C:10]2[C:17]1[N:22]=[C:21]2[C:23]([C:45]([O:47]C)=[O:46])=[CH:24][N:25]([C:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:20]2=[N:19][CH:18]=1.[OH-].[K+]>O.O1CCOCC1>[NH2:1][C:2]([CH3:50])([CH3:49])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[N:11]=[C:10]2[C:17]1[N:22]=[C:21]2[C:23]([C:45]([OH:47])=[O:46])=[CH:24][N:25]([C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:20]2=[N:19][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 71279592methyl 2-(5-(4-amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate

Product 1

HCID 712808552-(5-(4-Amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acidYield 102.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 31275
1,4-Dioxane
Solvent

Procedure

A mixture of methyl 2-(5-(4-amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylate (100 mg, 0.15 mmol), potassium hydroxide (280 mg, 5 mmol) in 2.5 mL of water and 5 mL of 1,4-dioxane was heated to reflux for 90 min. The reaction mixture was cooled to room temperature, solvent evaporated, the residue diluted with H2O (25 mL) and the mixture acidified with 1N HCl to pH=7. The residue was extracted with EtOAc (100 mL). The organic layer was washed with H2O (100 mL), brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure to give 2-(5-(4-Amino-4-methylpentyloxy)-1-methyl-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid as yellow solid (100 mg, >100%) which was used to next step without further purification. LCMS: (M+H)+=651.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 90 min
  3. customsolvent evaporated
  4. additionthe residue diluted with H2O (25 mL)
  5. extractionThe residue was extracted with EtOAc (100 mL)
  6. washThe organic layer was washed with H2O (100 mL), brine (100 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-afb2fa993e4740fd893ab0986969a06e
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658646B2

Reaction notes

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