Acetic Acid → 6-(3-fluorobenzyl)-1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid
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]Participants
5
Reactant 4
Product 1
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
- customAcOH was removed in vacuo
- dissolutionThe residue was dissolved in methanol (2 mL)
- customWhen the hydrolysis reaction
- filtrationit was filtered
- additiondiluted with MeCN and H2O
- custompurified via preparative HPLC-MS (C18
- washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)
Sources & evidence
- ORD record
- ord-e0ce42a56495472080a17b9b72765c97
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309246B2
Reaction notes
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