Pyridine → 2-({[6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carbonyl]-amino}-methyl)-morpholine-4-carboxylic acid tert-butyl ester

HRID 402045Notes

Reaction equation

HRID 402045 reaction equation
Cl.FC1C([O:9][C:10]([C:12]2[N:13]=[N:14][C:15]([CH2:31][CH2:32][CH2:33][CH3:34])=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:20][CH:19]=3)[CH:17]=2)=O)=C(F)C(F)=C(F)C=1F.N1C=CC=CC=1.[C:45]([O:49][C:50]([N:52]1[CH2:57][CH2:56][O:55][CH:54]([CH2:58][NH2:59])[CH2:53]1)=[O:51])([CH3:48])([CH3:47])[CH3:46]>C1COCC1>[C:45]([O:49][C:50]([N:52]1[CH2:57][CH2:56][O:55][CH:54]([CH2:58][NH:59][C:10]([C:12]2[N:13]=[N:14][C:15]([CH2:31][CH2:32][CH2:33][CH3:34])=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]4[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]4)=[CH:20][CH:19]=3)[CH:17]=2)=[O:9])[CH2:53]1)=[O:51])([CH3:48])([CH3:47])[CH3:46]

Participants

5

Reactant 3

HCID 1049PyridineHCID 19081094tert-Butyl 2-(aminomethyl)morpholine-4-carboxylateHCID 866578226-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid pentafluorophenyl ester hydrochloride

Product 1

HCID 673736352-({[6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carbonyl]-amino}-methyl)-morpholine-4-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid pentafluorophenyl ester hydrochloride (0.18 mmol, 0.1 g, Example 90) and 0.1 mL of pyridine in 2 mL of THF was added 2-aminomethyl-morpholine-4-carboxylic acid tert-butyl ester (0.4 mmol, 0.09 g). The mixture was shaken at room temperature, and upon completion of the reaction, the solvent was removed. The residue was chromatographed with 4% methanolic solution of ammonia (2.0 M ammonia in methanol) in EtOAc to provide 2-({[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carbonyl]-amino}-methyl)-morpholine-4-carboxylic acid tert-butyl ester. LCMS: m/z 553.0 [M+1].

Workup

  1. customupon completion of the reaction
  2. customthe solvent was removed
  3. customThe residue was chromatographed with 4% methanolic solution of ammonia (2.0 M ammonia in methanol) in EtOAc

Sources & evidence

ORD record
ord-d09698b0d2fc48b08db6544256c9135f
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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