Hydrochloric Acid → HCID 25122001, compound

HRID 383640Notes

Reaction equation

HRID 383640 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH:27]=[CH:28][CH:29]=1)[CH2:10][N:11]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]([C:18]2[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=2)[C:21](O)=[O:22])=[N:12]1)=[O:5])[CH3:2].Cl>C1COCC1>[CH2:1]([O:3][C:4](=[O:5])[NH:6][C:7]1[CH:29]=[CH:28][CH:27]=[C:9]([CH2:10][N:11]2[C:16](=[O:17])[CH:15]=[CH:14][C:13]([C:18]3[CH:26]=[CH:25][CH:24]=[C:20]([CH2:21][OH:22])[CH:19]=3)=[N:12]2)[CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59406753HCID 59406753, compound

Product 1

HCID 25122001HCID 25122001, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2 g (5.1 mmol) of 3-[1-(3-ethoxycarbonylaminobenzyl)-6-oxo-1,6-dihydropyridazin-3-yl]benzoic acid are suspended in 60 ml of THF, and 12.7 ml (12.7 mmol) of borane/THF complex (1M) are added dropwise under a nitrogen atmosphere with ice-cooling. The mixture is stirred at 0° C. for 15 h. 6 ml of 2N HCl are added to the reaction mixture, which is then stirred at room temperature for 12 h. The reaction mixture is evaporated, the residue is dissolved in ethyl acetate, dried over sodium sulfate and evaporated. The product is purified by means of preparative HPLC.

Workup

  1. addition12.7 ml (12.7 mmol) of borane/THF complex (1M) are added dropwise under a nitrogen atmosphere with ice-
  2. temperaturecooling
  3. stirringis then stirred at room temperature for 12 h
  4. customThe reaction mixture is evaporated
  5. dissolutionthe residue is dissolved in ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe product is purified by means of preparative HPLC

Sources & evidence

ORD record
ord-4dfee3264a614471800f45e93a814311
Source dataset
uspto-grants-2013_02
Patent number
US08367668B2

Reaction notes

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