Diisopropylethylamine → (4-{[6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carbonyl]-amino}-cyclohexyl)-carbamic acid tert-butyl ester

HRID 402053Notes

Reaction equation

HRID 402053 reaction equation
Cl.Cl.N1CCO[CH:5]([CH2:9][NH:10][C:11]([C:13]2[N:14]=[N:15][C:16]([CH2:32][CH2:33][CH2:34][CH3:35])=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]4)=[CH:21][CH:20]=3)[CH:18]=2)=[O:12])[CH2:4]1.[C:36]([O:40][C:41](=[O:50])[NH:42][C@H:43]1CC[C@@H](N)[CH2:45][CH2:44]1)([CH3:39])([CH3:38])[CH3:37].C(N(C(C)C)C(C)C)C>C1COCC1.C(OCC)C>[C:36]([O:40][C:41](=[O:50])[NH:42][CH:43]1[CH2:4][CH2:5][CH:9]([NH:10][C:11]([C:13]2[N:14]=[N:15][C:16]([CH2:32][CH2:33][CH2:34][CH3:35])=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH:26]4[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]4)=[CH:21][CH:20]=3)[CH:18]=2)=[O:12])[CH2:45][CH2:44]1)([CH3:39])([CH3:38])[CH3:37]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 673737226-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid (morpholin-2-ylmethyl)-amide dihydrochlorideHCID 178418966HCID 178418966, compound

Product 1

HCID 67373832(4-{[6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carbonyl]-amino}-cyclohexyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carboxylic acid pentafluorophenyl ester hydrochloride (Example 90, 0.234 mmol, 130 mg), (±)-(cis)-(4-amino-cyclohexyl)-carbamic acid tert-butyl ester (0.1 mL), ethyl-diisopropyl-amine (0.3 mL) in THF (2 mL) may be stirred for 3 h. The reaction mixture may be diluted with diethyl ether, washed with water and 2 M aq. sodium hydroxide solution and dried over magnesium sulfate. Purification by column chromatography on silica gel using 10-40% ethyl acetate in hexanes provides (4-{[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazine-3-carbonyl]-amino}-cyclohexyl)-carbamic acid tert-butyl ester.

Workup

  1. washwashed with water and 2 M aq. sodium hydroxide solution
  2. dry with materialdried over magnesium sulfate
  3. customPurification by column chromatography on silica gel using 10-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-79e714fe45d74611907802e0a5ec2fdd
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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