Acetic Acid → HCID 118159608, compound

HRID 628377Notes

Reaction equation

HRID 628377 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]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33]C(O)=O>>[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]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 118159647HCID 118159647, compound

Product 1

HCID 118159608HCID 118159608, compoundYield 40%

Procedure

di-tert-Butyl 1-(1-benzyl-1H-pyrazolo[4,3-b]pyridin-5-yl)hydrazine-1,2-dicarboxylate (0.030 g, 0.068 mmol, from Step 2) in AcOH (3 mL) was heated in the microwave to 180° C. for 5 minutes. The AcOH was removed in vacuo, the residue was reconstituted in MeOH, and purified via preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) to afford product (8 mg, 40%).

Workup

  1. customThe AcOH 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-a0a789973c8c428293d09294c688b994
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

Loading…