Triphenylphosphine → Ethyl{3-[3-(4-cyanophenyl)-6-oxo-6h-pyridazin-1-ylmethyl]phenyl}carbamate

HRID 383629Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12](=[O:15])[NH:13][N:14]=2)=[CH:5][CH:4]=1)#[N:2].[CH2:16]([O:18][C:19](=[O:29])[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27]O)[CH:22]=1)[CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:16]([O:18][C:19](=[O:29])[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][N:13]2[C:12](=[O:15])[CH:11]=[CH:10][C:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)=[N:14]2)[CH:22]=1)[CH3:17]

Participants

Conditions

Temperature: 0 °C

Procedure

15 g (76 mmol) of 6-(4-cyanophenyl)-2H-pyridazin-3-one, 22.2 g (114 mmol) of ethyl(3-hydroxymethylphenyl)carbamate and 29.9 g (114 mmol) of triphenylphosphine are dissolved in 250 ml of THF. Under a nitrogen atmosphere, the reaction mixture is cooled to 0° C., 18 ml (174 mmol) of diethyl azodicarboxylate are slowly added dropwise, and the reaction mixture is stirred at room temperature for 72 h. The reaction mixture is evaporated to dryness. 200 ml of isopropanol are added to the residue, and the mixture is stirred for 15 h. The precipitate is filtered off with suction, washed with isopropanol and dried in vacuo.

Workup

customThe reaction mixture is evaporated to dryness
addition200 ml of isopropanol are added to the residue
stirringthe mixture is stirred for 15 h
filtrationThe precipitate is filtered off with suction
washwashed with isopropanol
customdried in vacuo

Sources & evidence

ORD record: ord-19af525f0e0543f7b703c0bb79f02f39
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367668B2

Reaction notes

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