Dimethylformamide → HCID 66749947, compound

HRID 1747864Notes

Reaction equation

HRID 1747864 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2N(O)N=[N:7][C:5]=2C=1.CC[N:13]=[C:14]=[N:15]CCCN(C)C.Cl.[CH:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=O)=[CH:28][CH:27]=1)([CH3:25])[CH3:24].C(=O)([O-])O.[Na+].C[N:41](C=O)C>O>[CH3:25][CH:23]([C:26]1[CH:27]=[CH:28][C:29]([C:30]2[O:32][N:15]=[C:14]([C:4]3[C:5]([NH2:7])=[N:41][CH:1]=[CH:2][CH:3]=3)[N:13]=2)=[CH:33][CH:34]=1)[CH3:24]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 108204-Isopropylbenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 66749947HCID 66749947, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-amino-N′-hydroxypyridine-3-carboxyamide (1070 mg), HOBt.H2O (1185 mg), EDCI HCl (1483 mg) and 4-isopropylbenzoic acid (1270 mg) in dehydrated DMF (40 mL) was stirred at room temperature overnight and at 80° C. for 24 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (302 mg) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1ab71eddd2424f5fb80608fa1350e0c1
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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