Lithium hydroxide, monohydrate → HCID 11464383, compound

HRID 2056603Notes

Reaction equation

HRID 2056603 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:35])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[N:22]=[N:23][C:24]([C:27](=[O:34])[NH:28][CH2:29][CH2:30][CH:31]3[CH2:33][CH2:32]3)=[CH:25][CH:26]=2)[CH2:17][CH2:16]1)=[O:14]>O1CCCC1.O>[CH:31]1([CH2:30][CH2:29][NH:28][C:27]([C:24]2[N:23]=[N:22][C:21]([N:18]3[CH2:17][CH2:16][N:15]([C:13]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[C:6]([OH:35])=[O:5])=[O:14])[CH2:20][CH2:19]3)=[CH:26][CH:25]=2)=[O:34])[CH2:33][CH2:32]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 11166493HCID 11166493, compound

Product 1

HCID 11464383HCID 11464383, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (0.066 g, 1.57 mmol) was added to a solution of 2-{4-[6-(2-cyclopropylethylcarbamoyl)pyridazin-3-yl]piperazine-1-carbonyl}benzoic acid methyl ester (0.230 g) in tetrahydrofuran (10 mL) and water (5 mL) stirred at ambient temperature overnight. THF was removed in vacuo, the residue was dissolved in ethyl acetate (100 mL), neutralized by addition of 5% HCl solution, washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was recrystallized from dichloromethane and hexanes to yield 0.107 g of the title compound (42% yield). 1H NMR (300 MHz, CDCl3) δ 8.67, 9.07-7.87, 7.54, 7.41, 7.26-7.24, 6.95, 4.12-3.27, 1.55-1.40, 0.77-0.64, 0.50-0.34, 0.13-0.01; 13C NMR (75 MHz, CDCl3) δ 170.7, 168.2, 163.2, 159.9, 145.0, 137.7, 133.1, 131.2, 129.2, 127.9, 127.2, 126.6, 112.6, 46.2, 44.1, 41.4, 39.7, 34.4, 8.6, 4.2; MS (ES+) m/z 424.2 (M+1).

Workup

  1. customTHF was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  3. additionneutralized by addition of 5% HCl solution
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was recrystallized from dichloromethane and hexanes

Sources & evidence

ORD record
ord-62f48e026fa848cc9e78c16e02cdf57d
Source dataset
uspto-grants-2008_02
Patent number
US07335658B2

Reaction notes

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