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

HRID 383642ノート

反応式

HRID 383642 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8395318e044b4418ac2bb549f8fdd967
出典データセット
uspto-grants-2013_02
特許番号
US08367668B2

反応ノート

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