Triphenylphosphine → 4-[1-(1H-indazol-5-ylmethyl)-6-oxo-1,6-dihydropyridazin-3-yl]-N-(3-piperidin-1-ylpropyl)benzamide

HRID 383647Notes

Reaction equation

HRID 383647 reaction equation
[O:1]=[C:2]1[NH:7][N:6]=[C:5]([C:8]2[CH:25]=[CH:24][C:11]([C:12]([NH:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:13])=[CH:10][CH:9]=2)[CH:4]=[CH:3]1.[NH:26]1[C:34]2[C:29](=[CH:30][C:31]([CH2:35]O)=[CH:32][CH:33]=2)[CH:28]=[N:27]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[NH:26]1[C:34]2[C:29](=[CH:30][C:31]([CH2:35][N:7]3[C:2](=[O:1])[CH:3]=[CH:4][C:5]([C:8]4[CH:25]=[CH:24][C:11]([C:12]([NH:14][CH2:15][CH2:16][CH2:17][N:18]5[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]5)=[O:13])=[CH:10][CH:9]=4)=[N:6]3)=[CH:32][CH:33]=2)[CH:28]=[N:27]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 1514190(1H-indazol-5-yl)methanolHCID 594067824-(6-oxo-1,6-dihydropyridazin-3-yl)-N-(3-piperidin-1-ylpropyl)benzamide

Product 1

HCID 594067764-[1-(1H-indazol-5-ylmethyl)-6-oxo-1,6-dihydropyridazin-3-yl]-N-(3-piperidin-1-ylpropyl)benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 38 mg (0.11 mmol) of 4-(6-oxo-1,6-dihydropyridazin-3-yl)-N-(3-piperidin-1-ylpropyl)benzamide are suspended in 1 ml of THF, and 27 mg (0.18 mmol) of (1H-indazol-5-yl)methanol and 88 mg (0.34 mmol) of triphenyphosphine are added. 53 μl (0.34 mmol) of diethyl azodicarboxylate was added dropwise to this suspension at 2-10° C. with ice-cooling. The suspension was stirred at room temperature for 15 h. The reaction mixture was evaporated and purified by means of preparative HPLC.

Workup

  1. temperaturecooling
  2. customThe reaction mixture was evaporated
  3. custompurified by means of preparative HPLC

Sources & evidence

ORD record
ord-a80b5a8e85fc4e5d9c11f0b230ee01eb
Source dataset
uspto-grants-2013_02
Patent number
US08367668B2

Reaction notes

Loading…