Triphenylphosphine → Ethyl[3-(3-cyano-6-oxo-6H-pyridazin-1-ylmethyl)phenyl]-carbamate

HRID 383642Notes

Reaction equation

HRID 383642 reaction equation
[O:1]=[C:2]1[NH:7][N:6]=[C:5]([C:8]#[N:9])[CH:4]=[CH:3]1.[CH2:10]([O:12][C:13](=[O:23])[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21]O)[CH:16]=1)[CH3:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:10]([O:12][C:13](=[O:23])[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:7]2[C:2](=[O:1])[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6]2)[CH:16]=1)[CH3:11]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10607893Ethyl (3-hydroxymethylphenyl)carbamateHCID 226366116-Oxo-1,6-dihydropyridazine-3-carbonitrile

Product 1

HCID 59406667Ethyl[3-(3-cyano-6-oxo-6H-pyridazin-1-ylmethyl)phenyl]-carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 1 g (8.3 mmol) of 6-oxo-1,6-dihydropyridazine-3-carbonitrile (prepared in accordance with WO 2002/079200) is suspended in 50 ml of THF, and 2.4 g (12.4 mmol) of ethyl(3-hydroxymethylphenyl)carbamate and 5 g (12.4 mmol) of triphenyphosphine are added. 1.95 ml (12.4 mmol) of diethyl azodicarboxylate is added dropwise to this suspension at 2-10° C. with ice-cooling. The suspension is stirred at room temperature for 15 h. The suspension is filtered, and the filter residue is washed with dichloromethane, the filtrate is evaporated to dryness, taken up in ethyl acetate, and the organic phase is extracted with 1N HCl and saturated sodium hydrogencarbonate solution. The organic phase is subsequently dried over sodium sulfate and evaporated to dryness.

Workup

  1. temperaturecooling
  2. filtrationThe suspension is filtered
  3. washthe filter residue is washed with dichloromethane
  4. customthe filtrate is evaporated to dryness
  5. extractionthe organic phase is extracted with 1N HCl and saturated sodium hydrogencarbonate solution
  6. dry with materialThe organic phase is subsequently dried over sodium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-8395318e044b4418ac2bb549f8fdd967
Source dataset
uspto-grants-2013_02
Patent number
US08367668B2

Reaction notes

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