Hydrochloric Acid → HCID 135875967, compound

HRID 383643Notes

Reaction equation

HRID 383643 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]2[C:18](=[O:19])[CH:17]=[CH:16][C:15]([C:20]3[CH:25]=[CH:24][C:23]([C:26](=[NH:29])[NH:27][OH:28])=[CH:22][CH:21]=3)=[N:14]2)[CH:7]=1)[CH3:2].N1C=CC=CC=1.Cl[C:38](OCC)=[O:39].Cl>CN(C=O)C.O>[CH2:1]([O:3][C:4](=[O:30])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]2[C:18](=[O:19])[CH:17]=[CH:16][C:15]([C:20]3[CH:21]=[CH:22][C:23]([C:26]4[NH:29][C:38](=[O:39])[O:28][N:27]=4)=[CH:24][CH:25]=3)=[N:14]2)[CH:7]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10928Ethyl chloroformateHCID 178473429HCID 178473429, compound

Product 1

HCID 135875967HCID 135875967, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

500 mg (123 mmol) of ethyl(3-{3-[4-(N-hydroxycarbamimidoyl)phenyl]-6-oxo-6H-pyridazin-1-ylmethyl}phenyl)carbamate are dissolved in 20 ml of DMF, and 300 μl of pyridine are added. 128 μl (1.35 mmol) of ethyl chloroformate are subsequently added, and the solution is stirred at 100° C. for 24 h. 10 ml of 1 N HCl and water are added to the reaction mixture. The batch is evaporated to dryness, ethyl acetate is added, and the mixture is extracted with water. The organic phase is dried over sodium sulfate, evaporated to dryness and purified by means of preparative HPLC.

Workup

  1. customThe batch is evaporated to dryness, ethyl acetate
  2. additionis added
  3. extractionthe mixture is extracted with water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated to dryness
  6. custompurified by means of preparative HPLC

Sources & evidence

ORD record
ord-fde241111c0e4e8a81eb517c5c414ab4
Source dataset
uspto-grants-2013_02
Patent number
US08367668B2

Reaction notes

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