Acetic Acid → 1-methyl-6-(phenylsulfonyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid

HRID 628297Notes

Reaction equation

HRID 628297 reaction equation
C([O:5][C:6]([C:8]1[N:16]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:15]2[C:10](=[N:11][C:12]([N:26](C(OC(C)(C)C)=O)[NH:27][C:28](OC(C)(C)C)=O)=[CH:13][CH:14]=2)[CH:9]=1)=[O:7])(C)(C)C.[CH3:42]C(O)=O>>[CH3:42][C:28]1[N:11]2[C:10]3[CH:9]=[C:8]([C:6]([OH:5])=[O:7])[N:16]([S:17]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)(=[O:19])=[O:18])[C:15]=3[CH:14]=[CH:13][C:12]2=[N:26][N:27]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 118159681di-tert-butyl 1-[2-(tert-butoxycarbonyl)-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]hydrazine-1,2-dicarboxylate

Product 1

HCID 1181597591-methyl-6-(phenylsulfonyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid

Procedure

A solution of di-tert-butyl 1-[2-(tert-butoxycarbonyl)-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]hydrazine-1,2-dicarboxylate (0.430 g, 0.730 mmol, from Step 2) in AcOH (7 mL) was heated in the microwave to a temperature of 180° C. for 3 minutes. The solid product was isolated by filtration and air dried, and used without further purification. Yield: (0.106 g, 41%). LCMS (M+H)+: 357.1.

Workup

  1. customThe solid product was isolated by filtration and air
  2. customdried
  3. customused without further purification

Sources & evidence

ORD record
ord-847cb0406f70417f826cd51fdd7ccdee
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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