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Acetic Acid → 6-(3-fluorobenzyl)-1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid

HRID 628361
Notes
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Reaction equation

HRID 628361 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=1)[CH2:5][N:6]1[C:14]2[C:9](=[N:10][C:11]([N:15](C(OC(C)(C)C)=O)[NH:16]C(OC(C)(C)C)=O)=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:31]([O:33]CC1C=CC=C(F)C=1)=[O:32].[OH-].[Na+].O.[CH3:48][C:49](O)=O>>[F:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=1)[CH2:5][N:6]1[C:14]2[CH:13]=[CH:48][C:49]3[N:10]([C:11]([CH3:12])=[N:15][N:16]=3)[C:9]=2[CH:8]=[C:7]1[C:31]([OH:33])=[O:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 118159869di-tert-butyl 1-(1-(3-fluorobenzyl)-2-{[(3-fluorobenzyl)oxy]carbonyl}-1H-pyrrolo[3,2-b]pyridin-5-yl)hydrazine-1,2-dicarboxylate

Product 1

HCID 1181598066-(3-fluorobenzyl)-1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid

Procedure

A solution of di-tert-butyl 1-(1-(3-fluorobenzyl)-2-{[(3-fluorobenzyl)oxy]carbonyl}-1H-pyrrolo[3,2-b]pyridin-5-yl)hydrazine-1,2-dicarboxylate (0.33 g, 0.54 mmol, from Step 2) in AcOH (10 mL) was heated in portions, in the microwave, to 180° C. for 10 minutes each. The reactions were pooled and AcOH was removed in vacuo. The residue was dissolved in methanol (2 mL) and 1.0 M NaOH in water (10 mL, 10 mmol) was added. When the hydrolysis reaction was complete, it was filtered, diluted with MeCN and H2O and then purified via preparative HPLC-MS (C18 eluting with a gradient of MeCN/H2O containing 0.15% NH4OH). Yield: (0.17 g, 97%). LCMS (M+H)+: 325.3.

Workup

  1. customAcOH was removed in vacuo
  2. dissolutionThe residue was dissolved in methanol (2 mL)
  3. customWhen the hydrolysis reaction
  4. filtrationit was filtered
  5. additiondiluted with MeCN and H2O
  6. custompurified via preparative HPLC-MS (C18
  7. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-e0ce42a56495472080a17b9b72765c97
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09309246B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes