Hydrochloric Acid → HCID 59799774, compound

HRID 656532Notes

Reaction equation

HRID 656532 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.I.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C.[CH3:33][C:34]([CH3:54])([CH3:53])[C:35]([N:37]1[C:45]2[C:40](=[CH:41][C:42]([NH:46][CH:47]3[CH2:52][CH2:51][CH2:50][NH:49][CH2:48]3)=[CH:43][CH:44]=2)[CH:39]=[N:38]1)=[O:36].Cl>CN(C=O)C>[CH3:33][C:34]([CH3:54])([CH3:53])[C:35]([N:37]1[C:45]2[C:40](=[CH:41][C:42]([NH:46][CH:47]3[CH2:52][CH2:51][CH2:50][N:49]([C:6](=[O:8])[C:5]4[CH:9]=[CH:10][CH:11]=[C:3]([S:2][CH3:1])[CH:4]=4)[CH2:48]3)=[CH:43][CH:44]=2)[CH:39]=[N:38]1)=[O:36]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 2203293-(Methylthio)benzoic AcidHCID 59799768HCID 59799768, compoundHCID 86622977HCID 86622977, compound

Product 1

HCID 59799774HCID 59799774, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(methylthio)benzoic acid (200 mg, 1.2 mmol) in DMF (4.5 mL) was added in succession N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydroiodide (345 mg, 1.75 mmol) 1-hydroxybenzotriazole hydrate (186 mg, 1.2 mmol) and diisopropylethylamine (0.630 mL, 3.6 mmol). After stirring at room temperature for 10 min, 2,2-dimethyl-1-(5-(piperidin-3-ylamino)-1H-indazol-1-yl)propan-1-one (300 mg, 1.0 mmol) was added in one portion. The solution was stirred under a nitrogen atmosphere overnight. The solution was poured into 1.0 M HCl (20 mL), extracted twice with EtOAc, and the organic phases were washed with 10% NaOH, dried over Na2SO4 and evaporated. Chromatography of the residue on silica gel, eluting with EtOAc/heptane, gave the title compound as a pale yellow foam (240 mg, 53%).

Workup

  1. stirringThe solution was stirred under a nitrogen atmosphere overnight
  2. extractionextracted twice with EtOAc
  3. washthe organic phases were washed with 10% NaOH
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. washChromatography of the residue on silica gel, eluting with EtOAc/heptane

Sources & evidence

ORD record
ord-9bcf9f9727de4869b80cb83a523aa73c
Source dataset
uspto-grants-2011_12
Patent number
US08071779B2

Reaction notes

Loading…