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

HRID 628336Notes

Reaction equation

HRID 628336 reaction equation
C([O:3][C:4]([C:6]1[N:14](S(C2C=CC=CC=2)(=O)=O)[C:13]2[C:8](=[N:9][C:10]([N:24](C(OC(C)(C)C)=O)[NH:25][C:26](OC(C)(C)C)=O)=[CH:11][CH:12]=2)[CH:7]=1)=[O:5])C.[OH-].[Na+].[CH3:42]C(O)=O>>[CH3:42][C:26]1[N:9]2[C:8]3[CH:7]=[C:6]([C:4]([OH:3])=[O:5])[NH:14][C:13]=3[CH:12]=[CH:11][C:10]2=[N:24][N:25]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 118159434di-tert-butyl 1-[2-(ethoxycarbonyl)-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]hydrazine-1,2-dicarboxylate

Product 1

HCID 1369631101-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acidYield 50%

Conditions

Temperature
180 °C

Procedure

A solution of di-tert-butyl 1-[2-(ethoxycarbonyl)-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]hydrazine-1,2-dicarboxylate (2.11 g, 3.76 mmol, from Step 2) in AcOH (32 mL) was split into four portions and each was heated in the microwave to a temperature of 180° C. for 3 minutes. The reaction contents were pooled and the AcOH was removed in vacuo. The residue was azeotroped with toluene twice. The residue was reconstituted in EtOH (10 mL) and was treated with 1.0 M NaOH (10 mL, 10 mmol) overnight. Purification via preparative HPLC-MS (C18 eluting with a gradient of MeCN and H2O containing 0.15% NH4OH) afforded product (0.42 g, 50%).

Workup

  1. customThe reaction contents
  2. customthe AcOH was removed in vacuo
  3. customThe residue was azeotroped with toluene twice
  4. customPurification via preparative HPLC-MS (C18
  5. washeluting with a gradient of MeCN and H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-fa316873e4594f8ea6d0bc4103b6a891
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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