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

HRID 1842371Notes

Reaction equation

HRID 1842371 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([NH:15][CH2:16][C:17]([OH:19])=O)=[CH:11][CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)C1C=CC=CC=1.N1NC(=O)C=CC=1.Cl.[F:36][C:37]([F:52])([F:51])[C:38]1[CH:50]=[CH:49][CH:48]=[CH:47][C:39]=1[O:40][CH:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1>>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([NH:15][CH2:16][C:17](=[O:19])[N:44]2[CH2:43][CH2:42][CH:41]([O:40][C:39]3[CH:47]=[CH:48][CH:49]=[CH:50][C:38]=3[C:37]([F:36])([F:51])[F:52])[CH2:46][CH2:45]2)=[CH:11][CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 7498Benzyl BromideHCID 681533(2H)-PyridazinoneHCID 171780044-(2-(Trifluoromethyl)phenoxy)piperidine hydrochlorideHCID 66958017(2-Benzyl-3-oxo-2,3-dihydro-pyridazin-4-ylamino)-acetic acid

Product 1

HCID 509156762-Benzyl-4-{2-oxo-2-[4-(2-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethylamino}-2H-pyridazin-3-oneYield 30%

Procedure

Compound 48 is prepared from (2-benzyl-3-oxo-2,3-dihydro-pyridazin-4-ylamino)-acetic acid (obtained following the operating mode for 4e using benzyl bromide to alkylate nitrogen 2 of pyridazinone) and from intermediate 1a in base form, following synthesis method 2 (yield: 30%).

Workup

  1. customobtained
  2. customsynthesis method 2 (yield: 30%)

Sources & evidence

ORD record
ord-fd4a635ab60741fdbf8a0328b4df20a5
Source dataset
uspto-grants-2015_02
Patent number
US08946225B2

Reaction notes

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