Hydrochloric Acid → HCID 178460133, compound

HRID 450724Notes

Reaction equation

HRID 450724 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[NH2:8].Cl.[C:23]([NH:27][CH2:28][C:29](O)=O)(=[O:26])[CH2:24][CH3:25].ON1C2N=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH:19]([C:16]1[CH:17]=[CH:18][C:13]([S:10]([NH:9][C:4]2[CH:5]=[CH:6][C:7]3[NH:8][C:29]([CH2:28][NH:27][C:23](=[O:26])[CH2:24][CH3:25])=[N:1][C:2]=3[CH:3]=2)(=[O:12])=[O:11])=[CH:14][CH:15]=1)([CH3:21])[CH3:20]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 98681N-PropionylglycineHCID 181649HOAtHCID 67023917HCID 67023917, compound

Product 1

HCID 178460133HCID 178460133, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(3,4-diamino-phenyl)-4-isopropyl-benzenesulfonamide×HCl (500 mg, 1.32 mmol) in DMF (20 ml) at 0° C. was added propionylamino-acetic acid (170 mg, 1.32 mmol) and 1-hydroxy-7-azabenzotriazole (HOAt) (220 mg, 1.59 mmol). After stirring the mixture at 0° C. for 15 min EDC (N-ethyl-N′-(3-dimethylaminopropyl)-carbodiimide) (300 mg, 1.45 mmol) was added. DIPEA (diisopropylethylamine) (0.92 ml, 5.29 mmol) was added after stirring another 15 min at 0° C. The mixture was stirred at room temperature for 16 h, and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and saturated aqueous NaHCO3 and the organic layer was dried over MgSO4, filtered, and the solvent evaporated under reduced pressure. A solution of the obtained oil in acetic acid was heated to 70° C. for 6 h. After evaporation of the solvent in vacuo the residue was purified by column chromatography to give the product as a yellow oil (320 mg, 61%).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature for 16 h
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and saturated aqueous NaHCO3
  5. dry with materialthe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure
  8. temperatureA solution of the obtained oil in acetic acid was heated to 70° C. for 6 h
  9. customAfter evaporation of the solvent in vacuo the residue
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-8d9ad607050c481cb04f0423e2542194
Source dataset
uspto-grants-2013_07
Patent number
US08486984B2

Reaction notes

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