Sodium Hydroxide → HCID 178456377, compound

HRID 1984031Notes

Reaction equation

HRID 1984031 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([C@H:12]2[CH2:17][CH2:16][C@H:15]([O:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([NH:25][NH2:26])=[O:24])=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH:29]1([C:32](O)=O)[CH2:31][CH2:30]1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>>[CH:29]1([C:32]2[O:24][C:23]([C:22]3[CH:21]=[CH:20][C:19]([O:18][C@H:15]4[CH2:16][CH2:17][C@H:12]([C:10]([N:7]5[CH2:8][CH2:9][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6]5)=[O:11])[CH2:13][CH2:14]4)=[CH:28][CH:27]=3)=[N:25][N:26]=2)[CH2:31][CH2:30]1

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 15655Cyclopropanecarboxylic acidHCID 24813Phosphorus oxychlorideHCID 178456383HCID 178456383, compound

Product 1

HCID 178456377HCID 178456377, compoundYield 60.8%

Procedure

A mixture of 80 mg (0.21 mmol) of trans-4-[4-(4-Isopropyl-piperazine-1-carbonyl)-cyclohexyloxy]-benzoic acid hydrazide, 0.02 ml (0.26 mmol) of cyclopropanecarboxylic acid and 2 ml of phosphorus oxychloride was refluxed for 2 hr. To the mixture, 1N NaOH solution was added. The mixture was extracted with AcOEt, washed with saturated NaHCO3 solution, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica eluting with dichloromethane and methanol=from 98:2 to 19:1. The combined product fractions were evaporated to dryness to yield 56 mg (56%) of the title compound. MS (m/e): 439.4 (MH+).

Workup

  1. temperaturewas refluxed for 2 hr
  2. extractionThe mixture was extracted with AcOEt
  3. washwashed with saturated NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica eluting with dichloromethane and methanol=from 98:2 to 19:1
  7. customThe combined product fractions were evaporated to dryness

Sources & evidence

ORD record
ord-949fef71d77342398dec5c77d55b3d74
Source dataset
uspto-grants-2009_06
Patent number
US07544683B2

Reaction notes

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