Acetic Acid → US9777003, Example 1

HRID 628247Notes

Reaction equation

HRID 628247 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)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33](O)(=O)C>>[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][C:13]3[N:12]([C:19]([CH3:33])=[N:18][N:17]=3)[C:11]=2[CH:10]=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 118159423di-tert-butyl 1-(1-benzyl-1H-pyrrolo[3,2-b]pyridin-5-yl)hydrazine-1,2-dicarboxylate

Product 1

HCID 118159438US9777003, Example 1Yield 65%

Procedure

di-tert-Butyl 1-(1-benzyl-1H-pyrrolo[3,2-b]pyridin-5-yl)hydrazine-1,2-dicarboxylate (31 mg, 0.071 mmol, from Step 2) in acetic acid (4.0 mL) was heated in the microwave to 180° C. for 5 minutes. The solvent was removed in vacuo and the mixture was reconstituted in MeOH and purified using preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) and the eluent was frozen and lyophilized to afford a white powder (12 mg, 65%).

Workup

  1. customThe solvent was removed in vacuo
  2. custompurified
  3. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH) and the eluent
  4. temperaturewas frozen

Sources & evidence

ORD record
ord-978f536656c44f28853e1070efde45ea
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

Loading…