Acetic Acid → US9777003, Example 155

HRID 628367Notes

Reaction equation

HRID 628367 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=1)[CH2:5][N:6]1[C:14]2[C:9](=[N:10][C:11]([N:15](C(OC(C)(C)C)=O)[NH:16][C:17](OC(C)(C)C)=O)=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:31]1[N:35](C2CCCCO2)[N:34]=[CH:33][CH:32]=1.[CH3:45]C(O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:42]=[CH:43][CH:44]=1)[CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][C:11]3[N:10]([C:17]([CH3:45])=[N:16][N:15]=3)[C:9]=2[CH:8]=[C:7]1[C:31]1[NH:35][N:34]=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 118159899di-tert-butyl 1-{1-(3-chlorobenzyl)-2-[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl]-1H-pyrrolo[3,2-b]pyridin-5-yl}hydrazine-1,2-dicarboxylate

Product 1

HCID 118159473US9777003, Example 155

Procedure

A solution of di-tert-butyl 1-{1-(3-chlorobenzyl)-2-[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl]-1H-pyrrolo[3,2-b]pyridin-5-yl}hydrazine-1,2-dicarboxylate (0.50 g, 0.72 mmol, from Step 4) in AcOH (20 mL) and was heated in the microwave to a temperature of 180° C. for 8 minutes. The AcOH was removed in vacuo and the product was purified via preparative HPLC-MS (C18 eluting with a gradient of MeCN/H2O containing 0.15% NH4OH). Yield (78 mg, 30%).

Workup

  1. customThe AcOH was removed in vacuo
  2. customthe product was purified via preparative HPLC-MS (C18
  3. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)
  4. customYield (78 mg, 30%)

Sources & evidence

ORD record
ord-4724ac3f63164b94a4e7b1962327ef33
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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