Acetic Acid → HCID 118159635, compound

HRID 628288Notes

Reaction equation

HRID 628288 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[N:12][C:13]([N:17](C(OC(C)(C)C)=O)[NH:18][C:19](OC(C)(C)C)=O)=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:34](O)(=O)C>>[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][C:13]3[N:12]([C:19]([CH3:34])=[N:18][N:17]=3)[C:11]=2[N:10]=[C:9]1[CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 118159584HCID 118159584, compound

Product 1

HCID 118159635HCID 118159635, compoundYield 59%

Conditions

Temperature
180 °C

Procedure

di-tert-Butyl 1-(1-benzyl-2-methyl-1H-imidazo[4,5-b]pyridin-5-yl)hydrazine-1,2-dicarboxylate (0.075 g, 0.16 mmol, from Step 3) was dissolved in acetic acid (3 mL) and was heated in the microwave to 180° C. for 5 minutes. Solvent was removed in vacuo, the crude product was reconstituted in MeCN and purified via preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) to afford product (27 mg, 59%).

Workup

  1. customSolvent was removed in vacuo
  2. custompurified via preparative HPLC-MS (Waters XBridge C18
  3. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-1d3a9aea3eca4b48ad25acfdec0b07cc
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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