Ammonium Acetate → 7-(1H-Indazol-5-yl)-5-methyl-2,3,4,7-tetrahydrothieno[3,2-b]pyridine-6-carbonitrile-1,1-dioxide

HRID 408550Notes

Reaction equation

HRID 408550 reaction equation
[S:1]1(=[O:8])(=[O:7])[CH2:5][CH2:4][C:3](=O)[CH2:2]1.[NH:9]1[C:17]2[C:12](=[CH:13][C:14](/[CH:18]=[C:19](/[C:22](=O)[CH3:23])\[C:20]#[N:21])=[CH:15][CH:16]=2)[CH:11]=[N:10]1.C([O-])(=O)C.[NH4+:29]>C(O)(=O)C>[NH:9]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]3[C:19]([C:20]#[N:21])=[C:22]([CH3:23])[NH:29][C:3]4[CH2:4][CH2:5][S:1](=[O:8])(=[O:7])[C:2]3=4)=[CH:15][CH:16]=2)[CH:11]=[N:10]1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5150067dihydrothiophen-3(2H)-one 1,1-dioxideHCID 66725268(2E)-2-(1H-Indazol-5-ylmethylidene)-3-oxobutanenitrile

Product 1

HCID 469112177-(1H-Indazol-5-yl)-5-methyl-2,3,4,7-tetrahydrothieno[3,2-b]pyridine-6-carbonitrile-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

127 mg (0.947 mmol) dihydrothiophen-3(2H)-one-1,1-dioxide, 266 mg (0.947 mmol) (2E)-2-(1H-indazol-5-ylmethylidene)-3-oxobutanenitrile (Example 8A) and 88 mg (1.136 mmol) ammonium acetate in acetic acid (5 ml) were heated to reflux overnight. After cooling, the mixture was evaporated to dryness, and the residue was purified by preparative RP-HPLC (acetonitrile/water gradient) to yield 16 mg (5% of th.) of the title compound.

Workup

  1. temperatureto reflux overnight
  2. temperatureAfter cooling
  3. customthe mixture was evaporated to dryness
  4. customthe residue was purified by preparative RP-HPLC (acetonitrile/water gradient)

Sources & evidence

ORD record
ord-2bc8ea5121704e49a42ab2d1caa86624
Source dataset
uspto-grants-2014_06
Patent number
US08759341B2

Reaction notes

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