HCID 71766083, compound → HCID 71766225, compound

HRID 403378Notes

Reaction equation

HRID 403378 reaction equation
ClC1N=NC(NC)=C(C2C=CC=CC=2)C=1.[Cl:16][C:17]1[N:22]=[N:21][C:20]([N:23]([CH3:40])[C:24](=[O:39])[C:25]2[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([S:35]([CH3:38])(=[O:37])=[O:36])[CH:26]=2)=[C:19]([C:41]2[CH:46]=[CH:45][C:44](F)=[CH:43][C:42]=2OC)[CH:18]=1>CCCCCCC.C(OCC)(=O)C>[Cl:16][C:17]1[N:22]=[N:21][C:20]([N:23]([CH3:40])[C:24](=[O:39])[C:25]2[CH:30]=[C:29]([C:31]([F:34])([F:32])[F:33])[CH:28]=[C:27]([S:35]([CH3:38])(=[O:36])=[O:37])[CH:26]=2)=[C:19]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 71766083HCID 71766083, compound2×HCID 866984786-chloro-N-methyl-4-phenylpyridazin-3-amine

Product 1

HCID 71766225HCID 71766225, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 1, from (6-chloro-4-phenyl-pyridazin-3-yl)-methyl-amine and 3-methanesulfonyl-5-trifluoromethyl-benzoic acid (example 1, intermediate d) after a reaction time of 18 hours and using a gradient of n-heptane:ethyl acetate (100:0 to 30:70) for the chromatographic purification. Another purification step using preparative HPLC (Gemini NX column) with a gradient of methanol:water with 0.05% formic acid (80:20 to 98:2) gave the desired compound as a colorless solid (20%). MS (ESI+): m/z=470.054 ([M+H]+).

Workup

  1. customfor the chromatographic purification
  2. customAnother purification step

Sources & evidence

ORD record
ord-e7337ea0e16c4a81881f3913ad10d58d
Source dataset
uspto-grants-2014_06
Patent number
US08748434B2

Reaction notes

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