1,2-Dichloroethane → HCID 178426727, compound

HRID 2113045Notes

Reaction equation

HRID 2113045 reaction equation
[CH2:1]([S:8]([NH:11][C:12]1[C:13](=[O:23])[N:14]([CH2:19][C:20]([OH:22])=O)[C:15]([CH3:18])=[CH:16][CH:17]=1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.[N:26]1[NH:27][CH:28]=[C:29]2[C:34]=1[CH2:33][CH2:32][CH:31]([NH2:35])[CH2:30]2.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>CN(C=O)C>[CH2:1]([S:8]([NH:11][C:12]1[C:13](=[O:23])[N:14]([CH2:19][C:20]([NH:35][CH:31]2[CH2:32][CH2:33][C:34]3[C:29](=[CH:28][NH:27][N:26]=3)[CH2:30]2)=[O:22])[C:15]([CH3:18])=[CH:16][CH:17]=1)(=[O:9])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 154582213-Benzylsulfonylamino-6-methyl-1-carboxymethyl-2-pyridinoneHCID 1784786534,5,6,7-tetrahydro-1H-indazol-5-amine dihydrochloride

Product 1

HCID 178426727HCID 178426727, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[3-[(benzylsulfonyl)amino]-6-methyl-2-oxo-1(2H)-pyridinyl]acetic acid (94.1 mg, 0.28 mmol) and 4,5,6,7-tetrahydro-2H-indazol-5-ylamine dihydrochloride (58.8 mg, 0.28 mmol) in 1 mL of DMF was added HOBt (42.8 mg, 0.28 mmol). The pH of the solution was adjusted to 8 with N-methylmorpholine and EDC (53.7 mg, 0.28 mmol) was added. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated, and ethylacetate and saturated NaHCO3 solution were added to the residue. The water phase was extracted with ethyl acetate three times, and the combined organic phases were washed with saturated NaCl solution, dried over MgSO4, filtered and the solvent evaporated under reduced pressure. The product was purified by column chromatography (silicagel, eluant CH2Cl2/MeOH=9/1) to give 48 mg (38%) of a white solid compound.

Workup

  1. additionwas added
  2. customThe solvent was evaporated
  3. additionethylacetate and saturated NaHCO3 solution were added to the residue
  4. extractionThe water phase was extracted with ethyl acetate three times
  5. washthe combined organic phases were washed with saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure
  9. customThe product was purified by column chromatography (silicagel, eluant CH2Cl2/MeOH=9/1)

Sources & evidence

ORD record
ord-2ff7ddbf66af49bb9fd0d3b939db60d1
Source dataset
uspto-grants-2009_04
Patent number
US07524871B2

Reaction notes

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