Acetic Acid → US10442803, Example 2a

HRID 628251Notes

Reaction equation

HRID 628251 reaction equation
[CH3:1][C:2]1[N:10]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:9]2[C:4](=[N:5][C:6]([N:20](C(OC(C)(C)C)=O)[NH:21][C:22](OC(C)(C)C)=O)=[CH:7][CH:8]=2)[CH:3]=1.[CH3:36]C(O)=O>>[CH3:36][C:22]1[N:5]2[C:4]3[CH:3]=[C:2]([CH3:1])[N:10]([S:11]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)(=[O:12])=[O:13])[C:9]=3[CH:8]=[CH:7][C:6]2=[N:20][N:21]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 118159571di-tert-butyl 1-[2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]hydrazine-1,2-dicarboxylate

Product 1

HCID 118159509US10442803, Example 2a

Procedure

di-tert-Butyl 1-[2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]hydrazine-1,2-dicarboxylate (9.4 g, 19 mmol, from Step 3) in AcOH (150 mL) was heated in the range of 115-120° C. for 20 hours. Upon cooling to room temperature, the solvent was removed in vacuo. After this cyclization, purification via HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) afforded 1,7-dimethyl-6-(phenylsulfonyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine.

Workup

  1. customthe solvent was removed in vacuo
  2. customAfter this cyclization, purification via HPLC-MS (Waters XBridge C18
  3. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-a3ce9c87621444078e8090680e0aa553
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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