Acetic Acid → US9777003, Example 63

HRID 628309Notes

Reaction equation

HRID 628309 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(OC(C)(C)C)=O)=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:33]1[CH:34]=[N:35][N:36](C2CCCCO2)[CH:37]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:44][C:45](O)=O>>[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][C:13]3[N:12]([C:44]([CH3:45])=[N:18][N:17]=3)[C:11]=2[CH:10]=[C:9]1[C:33]1[CH:34]=[N:35][NH:36][CH:37]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 118159619di-tert-butyl 1-{1-benzyl-2-[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]-1H-pyrrolo[3,2-b]pyridin-5-yl}hydrazine-1,2-dicarboxylate

Product 1

HCID 136963112US9777003, Example 63

Procedure

di-tert-Butyl 1-{1-benzyl-2-[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]-1H-pyrrolo[3,2-b]pyridin-5-yl}hydrazine-1,2-dicarboxylate (68 mg, 0.12 mmol, from Step 2) in AcOH (4 mL) was heated in the microwave to 180° C. for 9 minutes. The acetic acid was removed in vacuo, and the residue was reconstituted in MeOH and purified via preparative HPLC-MS (C18 eluting with a gradient of MeCN and H2O containing 0.15% NH4OH). Yield: (17 mg, 45%).

Workup

  1. customThe acetic acid was removed in vacuo
  2. custompurified via preparative HPLC-MS (C18
  3. washeluting with a gradient of MeCN and H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-cc9ccadceba0455ab76d749f34057be5
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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