Isopropyl iodide → 2-Isopropyl-4-{2-oxo-2-[4-(2-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethylamino}-2H-pyridazin-3-one

HRID 1842372Notes

Reaction equation

HRID 1842372 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[C:8]([NH:11][CH2:12][C:13]([OH:15])=O)=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].IC(C)C.N1NC(=O)C=CC=1.Cl.[F:28][C:29]([F:44])([F:43])[C:30]1[CH:42]=[CH:41][CH:40]=[CH:39][C:31]=1[O:32][CH:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1>>[CH:1]([N:4]1[C:9](=[O:10])[C:8]([NH:11][CH2:12][C:13](=[O:15])[N:36]2[CH2:35][CH2:34][CH:33]([O:32][C:31]3[CH:39]=[CH:40][CH:41]=[CH:42][C:30]=3[C:29]([F:28])([F:43])[F:44])[CH2:38][CH2:37]2)=[CH:7][CH:6]=[N:5]1)([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 6362Isopropyl iodideHCID 681533(2H)-PyridazinoneHCID 171780044-(2-(Trifluoromethyl)phenoxy)piperidine hydrochlorideHCID 66957963(2-Isopropyl-3-oxo-2,3-dihydro-pyridazin-4-ylamino)-acetic acid

Product 1

HCID 509160032-Isopropyl-4-{2-oxo-2-[4-(2-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethylamino}-2H-pyridazin-3-oneYield 69%

Procedure

Compound 49 is prepared from (2-isopropyl-3-oxo-2,3-dihydro-pyridazin-4-ylamino)-acetic acid (obtained following the operating mode for 4e using 2-iodo-propane to alkylate nitrogen 2 of pyridazinone) and from intermediate 1a in base form, following synthesis method 2 (yield: 69%).

Workup

  1. customobtained
  2. customsynthesis method 2 (yield: 69%)

Sources & evidence

ORD record
ord-66c8206aeb9e4e0aba2d7a65d3d445f0
Source dataset
uspto-grants-2015_02
Patent number
US08946225B2

Reaction notes

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